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Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
10:00 am to 12:00 pm
The Oskaloosa Art Center Christmas Open House @RE/MAX Pride
4:00 pm to 7:00 pm
RE/MAX Pride
Christmas Open House @RE/MAX Pride
103 High Ave EastOskaloosa, IA
Map to Event
December 1, 2025
4:00 pm · 7:00 pm
You're Invited to Our Christmas Open House!
Hosted by REMAX Pride Real Estate
✨ Join us for a kickoff to the Christmas Holiday!
Date: Monday, December 1st
Time: 4:00 PM – 7:00 PM
First Stop: 103 High Ave East – main office
Second Stop: 1201 N Market St. - Dealmaker Lounge
What to Expect:
• Holiday treats & festive cocktails
• Agent office decorating contest
• Raffle prizes & giveaways
• Christmas Selfie Station courtesy of Snapshot Socials
Bring your friends, family, and holiday cheer! Whether you're buying, selling, or just browsing, we’d love to celebrate with you.
6:00 pm
Penn Central Mall
Young Ambassador Ceremony
Penn Central MallOskaloosa, IA
Map to Event
December 1, 2025
6:00 pm
The Young Ambassador Contest is back! One young man and one young lady will once again be chosen as Oskaloosa's young ambassadors. The winner will be determined by the amount of money raised, which will be used for local preschools & daycares along with the Lighted Christmas Parade
The king and queen will be announced on Monday, December 1 @ 6:00 pm in Penn Central Mall. All participants will receive great prizes and will have the opportunity to participate in the "Holiday Joys and Toys" Lighted Christmas Parade on Saturday, Dec. 6 at 7pm.
Link to 2025 Application
Contact: Amelia Boender
events@mahaskachamber.org
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
9:30 am to 2:00 pm
Oskaloosa High School Wine Tasting at Rosso & Wine
5:00 pm to 7:00 pm
Rosso & Wine
Wine Tasting at Rosso & Wine
Penn Central Mall - 200 High Avenue WestOskaloosa, IA
Map to Event
December 2, 2025
5:00 pm · 7:00 pm
Enjoy some Wine Tasting at Rosso & Wine.
For More Information(641) 676-8466
5:00 pm
Sunnyslope Greenhouse
Sparkle, Frost, Bling
Oskaloosa, IADecember 2, 2025
5:00 pm
5:30 pm to 7:30 pm
The Oskaloosa Art Center Bingo @the Eagles
6:30 pm
The Eagles
Bingo @the Eagles
215 High Ave EastOskaloosa, IA
Map to Event
December 2, 2025
6:30 pm
Bingo at the Eagles starting at 6:30 PM
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
10:00 am to 12:00 pm
The Oskaloosa Art Center Men's Caregiver Support Group
10:30 am to 12:00 pm
Bridget's Public House
Men's Caregiver Support Group
208 1st Ave EastOskaloosa, IA
Map to Event
December 3, 2025
10:30 am · 12:00 pm
We are a group of men navigating the role of primary caregivers for loved ones, gathering for coffee, conversation, and fellowship—whether sharing caregiving experiences or simply chatting about everyday topics (except politics). There are no reservations, fees, or obligations. Come as you are.
For More InformationContact: Rev. Molly Goodrich
(641) 673-4671
5:30 pm to 6:45 pm
The Oskaloosa Art Center
Drawn Together
Oskaloosa, IADecember 3, 2025
5:30 pm · 6:45 pm
7:00 pm
George Daily
The Best Christmas Pageant Ever
Oskaloosa, IADecember 3, 2025
7:00 pm
Wednesday-Sunday, Dec. 3-7
7 PM, Sat. and Sun. matinees
A George Daily Auditorium Production, featuring regional directors, designers, and performers
In this holiday classic adapted from the bestselling young adult book, a mother struggling to put on a church Christmas pageant is faced with casting the Herdman kids, the most awful kids in the history of the world!
But she and her community watch in surprise as the same old Christmas story is rejuvenated by the creativity, energy, and unexpected sincerity of a misunderstood young family.
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
5:00 pm
Sunnyslope Greenhouse
Winter in the Country
Oskaloosa, IADecember 4, 2025
5:00 pm
6:00 pm to 8:00 pm
Full Bloom Brewhouse
Full Bloom Music Bingo
1718 Pella AveOskaloosa, IA
Map to Event
December 4, 2025
6:00 pm · 8:00 pm
Join us Wednesday, December 4th at 6 PM for a FREE Music Bingo experience! You’ll get bingo cards filled with song titles, listen along as the DJ plays hits from every era, and mark your way to a win!
For More InformationContact: John
(641) 799-6437
brewer@fullbloombrewhouse.com
Website
6:30 pm to 7:30 pm
Penn Central Mall
Bethlehem's Joy/ Gospel Concert
Oskaloosa, IADecember 4, 2025
6:30 pm · 7:30 pm
7:00 pm
George Daily
The Best Christmas Pageant Ever
Oskaloosa, IADecember 3, 2025
7:00 pm
Wednesday-Sunday, Dec. 3-7
7 PM, Sat. and Sun. matinees
A George Daily Auditorium Production, featuring regional directors, designers, and performers
In this holiday classic adapted from the bestselling young adult book, a mother struggling to put on a church Christmas pageant is faced with casting the Herdman kids, the most awful kids in the history of the world!
But she and her community watch in surprise as the same old Christmas story is rejuvenated by the creativity, energy, and unexpected sincerity of a misunderstood young family.
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
9:00 am to 10:00 am
Environmental Learning Center
Coffee Club
Oskaloosa, IADecember 5, 2025
9:00 am · 10:00 am
Drop in and join us for fresh coffee and tasty treats during Coffee Club. We have fun talking about upcoming programs, volunteer opportunities with Mahaska County Conservation, and about everything in nature.
This month, bring a coffee cup or mug that is decorated for Christmas to take part in a door prize.
Registration is NOT needed, and we meet upstairs in the Discovery Lab.
10:00 am to 5:00 pm
Stepping Stones & Eagle's Nest Christian Bookstores
Book Signing with Children's Author Kay Fuller
117 S Market StOskaloosa, IA
Map to Event
December 5, 2025
10:00 am · 5:00 pm
5:00 pm to 8:00 pm
Various Locations
Holiday Tour of Homes
Oskaloosa, IADecember 5, 2025
5:00 pm · 8:00 pm
Annual Sieda Holiday Tour of Homes
5:00 pm to 8:00 pm
Tassel Ridge Winery
Wine & Pizza Night by Reservation Only
Oskaloosa, IADecember 5, 2025
5:00 pm · 8:00 pm
5:00–8:00 p.m.—Pizza served until 7:30 p.m.
Enjoy a glass of Tassel Ridge wine ($6–$12) with your favorite individual Wood Fired Oven Pizza ($15). Choose an Apple Bacon Cheddar Pizza; a Chicken, Spinach, Artichoke Heart, Black Olive, Shredded Mozzarella, and Roasted Garlic Cream Sauce (no Tomato Sauce) Pizza; a Margherita Pizza with Fresh Basil and Fresh Mozzarella; a Pepperoni, Black Olive, and Shredded Mozzarella Pizza; or select any four toppings from the Toppings of the Day (Apple, Artichoke Hearts, Bacon, Black Olives, Chicken, Fresh Basil, Fresh Mozzarella, Pepperoni, Roasted Garlic Cream Sauce, Shredded Mozzarella, Spinach) to Create Your Own Pizza ($17) and pair it with a Caesar Side Salad with Romaine, Croutons, Shredded Parmesan, and Caesar Dressing ($6). End your evening on a sweet note with a Chocolate Marshmallow Delight Pizza with Dark Chocolate, Milk Chocolate, and White Chocolate Chips and Marshmallows ($10). Seating is limited.
Seated Tastings, by Reservation only, will be available to enjoy before your meal. Our Seated Tastings include your choice of one of nine Tasting Flights. Flights include five wines, freshly baked bread, Frisian Farms Young Gouda, and Tassel Ridge® Dipping Oil. $15/$20 per flight.
Call the Winery at 641.672.WINE (9463) to make your reservations.
5:30 pm to 7:00 pm
Harry L. Anderson American Legion Post 34
Steak Night
Oskaloosa, IADecember 5, 2025
5:30 pm · 7:00 pm
Come join us for 12 oz. hand cut Ribeye, Baked Potato and house salad $23 OR 16oz whole catfish, baked potato and house salad $14 or 8 piece butterfly shrimp, baked potato and house salad $14. Entertainment is the Smalltown Super Hero's 7-10 pm. Everyone welcome.
7:00 pm
George Daily
The Best Christmas Pageant Ever
Oskaloosa, IADecember 3, 2025
7:00 pm
Wednesday-Sunday, Dec. 3-7
7 PM, Sat. and Sun. matinees
A George Daily Auditorium Production, featuring regional directors, designers, and performers
In this holiday classic adapted from the bestselling young adult book, a mother struggling to put on a church Christmas pageant is faced with casting the Herdman kids, the most awful kids in the history of the world!
But she and her community watch in surprise as the same old Christmas story is rejuvenated by the creativity, energy, and unexpected sincerity of a misunderstood young family.
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
8:00 am to 1:00 pm
Mahaska Drug
Christmas Scavenger Hunt Extravaganza
Oskaloosa, IADecember 6, 2025
8:00 am · 1:00 pm
10:00 am to 4:00 pm
Stella's Salon and Boutique
9th Anniversary Christmas Stellabration
Oskaloosa, IADecember 6, 2025
10:00 am · 4:00 pm
Prizes, refreshments, & more
10:00 am to 7:00 pm
Eagle's Nest Christian Bookstore
Book signing w/ Heather Fry
Oskaloosa, IADecember 6, 2025
10:00 am · 7:00 pm

10:00 am to 7:00 pm
Eagle's Nest Christian Bookstore
Christmas Open House
117 S Market StreetOskaloosa, IA
Map to Event
December 6, 2025
10:00 am · 7:00 pm
Come early to shop and then go to the Lighted Parade. We are open until 7pm!
For More InformationContact: Mindy Uitermarkt
(641) 673-8776
gteam@steppingstonesbookstores.com
Website
11:00 am
George Daily
The Best Christmas Pageant Ever
Oskaloosa, IADecember 6, 2025
11:00 am
Wednesday-Sunday, Dec. 3-7
7 PM, Sat. and Sun. matinees
A George Daily Auditorium Production, featuring regional directors, designers, and performers
In this holiday classic adapted from the bestselling young adult book, a mother struggling to put on a church Christmas pageant is faced with casting the Herdman kids, the most awful kids in the history of the world!
But she and her community watch in surprise as the same old Christmas story is rejuvenated by the creativity, energy, and unexpected sincerity of a misunderstood young family.
12:00 pm to 4:00 pm
Various Locations
Holiday Tour of Homes
Oskaloosa, IADecember 6, 2025
12:00 pm · 4:00 pm
Annual Sieda Holiday Tour of Homes
6:00 pm
1st Presbyterian Church
Parade warm up for marching band
Oskaloosa, IADecember 6, 2025
6:00 pm
7:00 pm
Downtown Oskaloosa
Annual Oskaloosa Lighted Christmas Parade
222 1st Ave. EastOskaloosa, IA
Map to Event
December 6, 2025
7:00 pm
Parade and Shuttle Route Maps to be updated for 2025! Check back for details.
Join us for the 38th Annual Lighted Christmas Parade. This year's theme is "Holiday Joys & Toys". You've seen the Painting with Lights in Oskaloosa, come check out the creativity of the parade entries with all the colors and lights.
The weeklong festivities will include the Young Ambassador Contest, Window Decorating, Home Decorating contests, Gospel Christmas Concert, Merry Little Downtown Christmas and more. We welcome the community to invite family, friends and visitors to make a trip to Oskaloosa.
As you visit the town, you can always get hot cocoa, apple cider or that warm Christmas cup of coffee at the local coffee shop; visit the Alley, decorated for the holiday; visit the quaint little bookstore for a Christmas read; or shop unique shops along the square for that perfect Christmas gift. Come see the lights, grab your cameras, and come celebrate Christmas in Oskaloosa.
For More InformationContact: Oskaloosa Main Street
(641) 672-2591
mainstreet@mahaskachamber.org
7:00 pm
George Daily
The Best Christmas Pageant Ever
Oskaloosa, IADecember 3, 2025
7:00 pm
Wednesday-Sunday, Dec. 3-7
7 PM, Sat. and Sun. matinees
A George Daily Auditorium Production, featuring regional directors, designers, and performers
In this holiday classic adapted from the bestselling young adult book, a mother struggling to put on a church Christmas pageant is faced with casting the Herdman kids, the most awful kids in the history of the world!
But she and her community watch in surprise as the same old Christmas story is rejuvenated by the creativity, energy, and unexpected sincerity of a misunderstood young family.
8:00 pm to 12:00 am
The Eagles
Jack @The Eagles
Oskaloosa, IADecember 6, 2025
8:00 pm · 12:00 am
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
2:00 pm
George Daily
The Best Christmas Pageant Ever
Oskaloosa, IADecember 7, 2025
2:00 pm
Wednesday-Sunday, Dec. 3-7
7 PM, Sat. and Sun. matinees
A George Daily Auditorium Production, featuring regional directors, designers, and performers
In this holiday classic adapted from the bestselling young adult book, a mother struggling to put on a church Christmas pageant is faced with casting the Herdman kids, the most awful kids in the history of the world!
But she and her community watch in surprise as the same old Christmas story is rejuvenated by the creativity, energy, and unexpected sincerity of a misunderstood young family.
3:00 pm to 5:00 pm
Tassel Ridge Winery
Wine & Canvas by Reservation Only
Oskaloosa, IADecember 7, 2025
3:00 pm · 5:00 pm
3:00–5:00 p.m.
Paint your very own Winter-themed masterpiece in acrylics under the guidance of Iowa artist Dora Olson. Gather a group of friends or make it a date night and have some fun creating your own art!
$50 per person, plus tax (includes one canvas, paint, instruction, Frisian Farms Gouda Cheese and Bread, and one glass of wine – Wine Recommendation 2022 Iowa Steuben).
Advance prepaid, non-refundable reservations required. Call the Winery at 641.672.WINE (9463) to make your reservations.
4:00 pm to 7:00 pm
Bethel Baptist Church
Cookies and a Christmas Movie
1407 A Ave WestOskaloosa, IA
Map to Event
December 7, 2025
4:00 pm · 7:00 pm
come watch King of Kings FREE at Bethel to welcome the Christmas season! we''ll have cookies and hot cocoa. Nursery staff available for kids under 3. Parents please attend with your children.
For More InformationContact: Ronnie Hemsworth
(641) 673-7623
Website
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
10:00 am to 12:00 pm
The Oskaloosa Art Center NAMI Family Support Group
5:00 pm to 6:00 pm
Zoom & Centerville
NAMI Family Support Group
209 E. Maple St.Centerville, IA
Map to Event
December 8, 2025
5:00 pm · 6:00 pm
NAMI Family Support Group is for any adult with a loved one who has experienced symptoms of a mental health condition. This group meets on the 2nd and 4th Monday of each month from 5 p.m.- 6 p.m. via Zoom and in person at the Optimae Building (209 E. Maple St) in Centerville. All of our support groups are free, confidential, and open to any member of our community over the age of 18. To sign up or for questions, please email us at info@namiscia.org or call/text 64-216-3114. We hope to see you there!
For More InformationContact: NAMI South Central Iowa
(641) 216-3114
info@namiscia.org
Website
6:00 pm to 7:30 pm
The Oskaloosa Art Center
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
5:00 pm to 7:00 pm
Rosso & Wine
Wine Tasting at Rosso & Wine
Penn Central Mall - 200 High Avenue WestOskaloosa, IA
Map to Event
December 9, 2025
5:00 pm · 7:00 pm
Enjoy some Wine Tasting at Rosso & Wine.
For More Information(641) 676-8466
5:15 pm to 6:00 pm
Zoom
NAMI Connection Support Group
December 9, 2025
5:15 pm · 6:00 pm
NAMI Connection Support Group is for any adult who has experienced symptoms of a mental health condition. All our support groups are free, confidential, and open to any member of our community over the age of 18. NAMI Connection Support Group meets on the 2nd & 4th Tuesday of the month from 5:15 p.m. until 6:15 p.m. via Zoom. To sign up or for questions, please email us at info@namiscia.org or call/text 64-216-3114. We hope to see you there!
For More InformationContact: NAMI South Central Iowa
(641) 216-3114
info@namiscia.org
Website
5:30 pm to 7:30 pm
The Oskaloosa Art Center Bingo @the Eagles
6:30 pm
The Eagles
Bingo @the Eagles
215 High Ave EastOskaloosa, IA
Map to Event
December 9, 2025
6:30 pm
Bingo at the Eagles starting at 6:30 PM
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
11:00 am to 1:00 pm
United Way of Mahaska County Office
Cookies & Cocoa
Oskaloosa, IADecember 10, 2025
11:00 am · 1:00 pm
You’re invited! Join United Way of Mahaska County for Cookies & Cocoa — a cozy community gathering to celebrate the season together.
Come enjoy sweet treats, warm cocoa, and holiday cheer with friends and neighbors!
Date: December 10th
Location: United Way of Mahaska County - 102 1st Ave E, Oskaloosa
Time: 11:00 am - 1:00 pm
All are welcome!![]()
6:00 pm to 7:30 pm
Full Bloom Brewhouse
Music Bingo
Oskaloosa, IADecember 10, 2025
6:00 pm · 7:30 pm
Each song played is a change to win!
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
5:00 pm to 7:00 pm
Mahaska Drug
Deck the Halls w/ BINGO Calls
Oskaloosa, IADecember 11, 2025
5:00 pm · 7:00 pm
5:30 pm to 6:30 pm
Oskaloosa YMCA
Sharing our Strength
1521 Green StreetOskaloosa, IA
Map to Event
December 11, 2025
5:30 pm · 6:30 pm
Join the Mahaska Health Oncology Care Team for "Sharing our Strength", a support group for those in our community who have been affected by cancer.
For More InformationContact: Oncology Care Team
(641) 676-7283
oncologycareteam@mahaskahealth.org
Website
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
11:00 am
Debbie's Celebration Barn
Womens Holiday Luncheon
Oskaloosa, IADecember 12, 2025
11:00 am
Join Us December 12 for the Women's Holiday Luncheon. Tickets must be purchased in advance for $25 at the Mahaska Chamber.
11AM-11:30AM- Registration & Reception
11:30AM-1:00PM- Lunch, Program, & Giveaways
1:00 pm to 2:00 pm
Environmental Learning Center
O.W.L.S. – Cookie Decorating
Oskaloosa, IADecember 12, 2025
1:00 pm · 2:00 pm
Mahaska County Conservation invites adults of all ages to join the O.W.L.S. (Older, Wiser, Livelier Souls) program on Friday, December 12, from 1:00–2:00 pm for a festive afternoon of holiday cookie decorating.
Bring a friend and enjoy a cozy, creative time decorating homemade sugar cookies. We’ll have coffee, hot chocolate, plenty of cookies to sample, and lots of holiday cheer!
Reservations are required. Please call (641) 673-9327, email decook@mahaskacountyia.gov, or register online by noon on December 11. Use this link for online reservations: O.W.L.S. Program "Cookie Decorating" - Caldwell Park, Mahaska County, IA - MyCountyPark.com
6:00 pm to 8:00 pm
Oskaloosa Art Center
Art Uncorked
115 1st Ave WOskaloosa, IA
Map to Event
December 12, 2025
6:00 pm · 8:00 pm
Social Painting Class for Adults 18 years and Older.
Sip your favorite beverage and have fun painting a piece inspired by an example work of arte. You will receive easy step-by-step instructions and personal attention from a professional artist.
Register here. https://www.faceofmahaska.com/adult-classes
For More InformationContact: Oskaloosa Art Center
(641) 676-4694
faceofmahaska@gmail.com
Website
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
5:00 pm to 7:00 pm
Leighton Christian Reformed Church
Christmas Soup Supper
Oskaloosa, IADecember 13, 2025
5:00 pm · 7:00 pm
6:00 pm
Tassel Ridge Winery
Wine Dinner & Murder Mystery, by Reservation Only
Oskaloosa, IADecember 13, 2025
6:00 pm
6:00 p.m.—Casting Reception
6:30 p.m.—Dinner Seating & Show
Reservations Required by 3:00 p.m. on Thursday, December 11
Tassel Ridge® Winery is the place to be for wine, dinner, and mystery, when Jest Murder Mystery Co. presents Dead! Like Me. During the show, enjoy a three-course dinner that begins with a Mixed Green Salad with Apples, Feta Cheese, Pistachios and Balsamic Vinaigrette; Baked Ham with Tassel Ridge Finalé Iowa Red Cherry Sauce served with Wild Rice and Green Beans with Bacon; and White Chocolate Raspberry Cheesecake.
Here's a sneak peek at Dead! Like Me.
Welcome back to the land of the living! Why the welcome? Because you’re dead. That’s right, and you have been teleported to the land of the living for a union meeting of The Brotherhood of Obituary Occupants (BOO!).This show is for everyone already dead. That’s right. You’re a ghost,…and P.T. Barnum, who is up to his usual tricks, is trying to include you in his latest scheme! But what do you threaten a dad man with? However, someone finds a way to do him in. Who did it? The guy across the room? The lady across the table? Or…maybe…you? Regardless, we promise you a great time at, …Dead! Like Me!
$75 per person, plus tax—Harvest Club Member & 1 Guest: $70 per person, plus tax (includes dinner, show, wine paired with each course, and gratuity).
Advance prepaid, non-refundable reservations required by 3:00 p.m. on Thursday, December 11.
6:00 pm
Tassel Ridge Winery
Wine Dinner & Murder Mystery, by Reservation Only
Oskaloosa, IADecember 13, 2025
6:00 pm
6:00 p.m.—Casting Reception
6:30 p.m.—Dinner Seating & Show
Reservations Required by 3:00 p.m. on Thursday, December 11
Tassel Ridge® Winery is the place to be for wine, dinner, and mystery, when Jest Murder Mystery Co. presents Dead! Like Me. During the show, enjoy a three-course dinner that begins with a Mixed Green Salad with Apples, Feta Cheese, Pistachios and Balsamic Vinaigrette; Baked Ham with Tassel Ridge Finalé Iowa Red Cherry Sauce served with Wild Rice and Green Beans with Bacon; and White Chocolate Raspberry Cheesecake.
Here's a sneak peek at Dead! Like Me.
Welcome back to the land of the living! Why the welcome? Because you’re dead. That’s right, and you have been teleported to the land of the living for a union meeting of The Brotherhood of Obituary Occupants (BOO!).This show is for everyone already dead. That’s right. You’re a ghost,…and P.T. Barnum, who is up to his usual tricks, is trying to include you in his latest scheme! But what do you threaten a dad man with? However, someone finds a way to do him in. Who did it? The guy across the room? The lady across the table? Or…maybe…you? Regardless, we promise you a great time at, …Dead! Like Me!
$75 per person, plus tax—Harvest Club Member & 1 Guest: $70 per person, plus tax (includes dinner, show, wine paired with each course, and gratuity).
Advance prepaid, non-refundable reservations required by 3:00 p.m. on Thursday, December 11.
6:30 pm to 9:30 pm
Full Bloom Brewhouse
Live Music Jonas Magram
Oskaloosa, IADecember 13, 2025
6:30 pm · 9:30 pm
Live Music Jonas Magram
7:00 pm to 9:00 pm
Full Bloom Brewhouse
Party and Potluck with live music from the Mondeau Dukes
Oskaloosa, IADecember 13, 2025
7:00 pm · 9:00 pm
Party and Potluck with live music from the Mondeau Dukes
7:00 pm to 9:00 pm
Full Bloom Brewhouse
The Mondeau Dukes Unplugged at Full Bloom Brewhouse
1718 Pella AveOskaloosa, IA
Map to Event
December 13, 2025
7:00 pm · 9:00 pm
The Dukes are unpacking the acoustics for an intimate evening at Full Bloom Brewhouse! Plan to get there early.
For More InformationContact: John
(641) 799-6437
brewer@fullbloombrewhouse.com
Website
Mahaska Drug
YMCA Christmas Tree Fundraiser
205 N E StreetOskaloosa, IA
Map to Event
November 23, 2025
Mahaska Drug-Oskaloosa Monday through Friday 4:00 pm to 6:00 pm Saturday 10:00am to 6:00pm Sunday 12:00pm to 5:00pm Trees ranging from 5 foot tall to 9 foot tall Scotch Pine: $25 White Pine: $45-$60 Douglas Fir : $45-$75 Fraser Fir: $60-$130
For More InformationContact: Mahaska YMCA
(641) 673-8411
Website
10:00 am to 12:00 pm
The Oskaloosa Art Center Pop-Up Christmas Project
6:00 pm to 7:30 pm
The Oskaloosa Art Center
Pop-Up Christmas Project
115 1st Ave WOskaloosa, IA
Map to Event
December 15, 2025
6:00 pm · 7:30 pm
5:00 pm to 7:00 pm
Rosso & Wine
Wine Tasting at Rosso & Wine
Penn Central Mall - 200 High Avenue WestOskaloosa, IA
Map to Event
December 16, 2025
5:00 pm · 7:00 pm
Enjoy some Wine Tasting at Rosso & Wine.
For More Information(641) 676-8466
5:30 pm to 7:30 pm
The Oskaloosa Art Center Bingo @the Eagles
6:30 pm
The Eagles
Bingo @the Eagles
215 High Ave EastOskaloosa, IA
Map to Event
December 16, 2025
6:30 pm
Bingo at the Eagles starting at 6:30 PM
7:30 pm to 8:30 pm
Awakening Grace Free Virtual Support Group
Oskaloosa, IADecember 16, 2025
7:30 pm · 8:30 pm
Free Virtual Support Group for Pregnancy and Infant Loss.
Every 3rd Tuesday of the Month.
7:30 PM-8:30PM Via Zoom
Registration is required. To register, email awakeninggracefoundation@gmail.com
For More Information
awakeninggracefoundation@gmail.com
9:00 am to 10:00 am
Online-Zoom
Understanding Accounting Basics for Business
Oskaloosa, IADecember 17, 2025
9:00 am · 10:00 am
10:30 am to 12:00 pm
Bridget's Public House
Men's Caregiver Support Group
208 1st Ave EastOskaloosa, IA
Map to Event
December 17, 2025
10:30 am · 12:00 pm
We are a group of men navigating the role of primary caregivers for loved ones, gathering for coffee, conversation, and fellowship—whether sharing caregiving experiences or simply chatting about everyday topics (except politics). There are no reservations, fees, or obligations. Come as you are.
For More InformationContact: Rev. Molly Goodrich
(641) 673-4671
6:00 pm to 8:00 pm
Full Bloom Brewhouse
Full Bloom Music Bingo
1718 Pella AveOskaloosa, IA
Map to Event
December 18, 2025
6:00 pm · 8:00 pm
Join us Wednesday, December 18th at 6 PM for a FREE Music Bingo experience! You’ll get bingo cards filled with song titles, listen along as the DJ plays hits from every era, and mark your way to a win!
For More InformationContact: John
(641) 799-6437
brewer@fullbloombrewhouse.com
Website
7:00 pm
G&G Pronto/ Penn Central Mall
Italian Christmas Dinner Party
Oskaloosa, IADecember 18, 2025
7:00 pm
7:00 pm
G&G Pronto/ Penn Central Mall
Italian Christmas Dinner Party
Oskaloosa, IADecember 18, 2025
7:00 pm
5:00 pm to 8:00 pm
Tassel Ridge Winery
Wine Dinner & Murder Mystery, by Reservation Only
Oskaloosa, IADecember 19, 2025
5:00 pm · 8:00 pm
5:00–8:00 p.m.—Pizza served until 7:30 p.m.
Enjoy a glass of Tassel Ridge wine ($6–$12) with your favorite individual Wood Fired Oven Pizza ($15). Choose an Apple Bacon Cheddar Pizza; a Beef Taco Pizza with Cheddar, Lettuce, Black Olives, Tortilla Chips, Shredded Mozzarella, and House-Made Salsa; a Margherita Pizza with Fresh Basil and Fresh Mozzarella; a Pepperoni, Black Olive, and Shredded Mozzarella Pizza; or select any four toppings from the Toppings of the Day (Apple, Bacon, Beef Taco Meat, Black Olives, Cheddar, Fresh Basil, Fresh Mozzarella, House-Made Salsa, Lettuce, Pepperoni, Shredded Mozzarella, Tortilla Chips) to Create Your Own Pizza ($17) and pair it with a Caesar Side Salad with Romaine, Croutons, Shredded Parmesan, and Caesar Dressing ($6). End your evening on a sweet note with a Chocolate Marshmallow Delight Pizza with Dark Chocolate, Milk Chocolate, and White Chocolate Chips and Marshmallows ($10). Seating is limited.
Seated Tastings, by Reservation only, will be available to enjoy before your meal. Our Seated Tastings include your choice of one of nine Tasting Flights. Flights include five wines, freshly baked bread, Frisian Farms Young Gouda, and Tassel Ridge® Dipping Oil. $15/$20 per flight.
Call the Winery at 641.672.WINE (9463) to make your reservations.
Mahaska Drug
Christmas Bake Sale - Mahaska Drug
Oskaloosa, IADecember 20, 2025
5:00 pm to 12:00 am
The Eagles
Steak Night & Foxy
Oskaloosa, IADecember 20, 2025
5:00 pm · 12:00 am
Steak 5-7pm
Foxy 8pm-12am
6:30 pm to 9:30 pm
Full Bloom Brewhouse
Live Music Chris Hackley
Oskaloosa, IADecember 20, 2025
6:30 pm · 9:30 pm
Live Music Chris Hackley
6:30 pm to 9:00 pm
Full Bloom Brewhouse
Live Music at Full Bloom Chris Hackley
1718 Pella AveOskaloosa, IA
Map to Event
December 20, 2025
6:30 pm · 9:00 pm
Come out and support some local live music. #supportlocalmusic
For More InformationContact: John
(641) 799-6437
brewer@fullbloombrewhouse.com
Website
Mahaska Drug
Christmas Bake Sale - Mahaska Drug
Oskaloosa, IADecember 21, 2025
Mahaska Drug
Christmas Bake Sale - Mahaska Drug
Oskaloosa, IADecember 22, 2025
5:00 pm to 6:00 pm
Zoom & Centerville
NAMI Family Support Group
209 E. Maple St.Centerville, IA
Map to Event
December 22, 2025
5:00 pm · 6:00 pm
NAMI Family Support Group is for any adult with a loved one who has experienced symptoms of a mental health condition. This group meets on the 2nd and 4th Monday of each month from 5 p.m.- 6 p.m. via Zoom and in person at the Optimae Building (209 E. Maple St) in Centerville. All of our support groups are free, confidential, and open to any member of our community over the age of 18. To sign up or for questions, please email us at info@namiscia.org or call/text 64-216-3114. We hope to see you there!
For More InformationContact: NAMI South Central Iowa
(641) 216-3114
info@namiscia.org
Website
Mahaska Drug
Christmas Bake Sale - Mahaska Drug
Oskaloosa, IADecember 23, 2025
1:00 pm to 2:30 pm
Environmental Learning Center
Nature Documentary "Chimpanzee"
Oskaloosa, IADecember 23, 2025
1:00 pm · 2:30 pm
“Chimpanzee” is a heartwarming documentary that follows Oscar, a young chimp, as he grows and explores life in the African rainforest. Viewers will enjoy watching his playful curiosity, his bond with family, and the challenges he faces while learning to survive in the wild. This film offers a close, inspiring look at the world of chimpanzees and the importance of family.
Feel free to bring a drink and snack to this program. We will meet upstairs in the Discovery Lab.
Please sign up to watch this documentary by using this link: Nature Documentary "Chimpanzees" - Caldwell Park, Mahaska County, IA - MyCountyPark.com
5:00 pm to 7:00 pm
Rosso & Wine
Wine Tasting at Rosso & Wine
Penn Central Mall - 200 High Avenue WestOskaloosa, IA
Map to Event
December 23, 2025
5:00 pm · 7:00 pm
Enjoy some Wine Tasting at Rosso & Wine.
For More Information(641) 676-8466
5:15 pm to 6:00 pm
Zoom
NAMI Connection Support Group
December 23, 2025
5:15 pm · 6:00 pm
NAMI Connection Support Group is for any adult who has experienced symptoms of a mental health condition. All our support groups are free, confidential, and open to any member of our community over the age of 18. NAMI Connection Support Group meets on the 2nd & 4th Tuesday of the month from 5:15 p.m. until 6:15 p.m. via Zoom. To sign up or for questions, please email us at info@namiscia.org or call/text 64-216-3114. We hope to see you there!
For More InformationContact: NAMI South Central Iowa
(641) 216-3114
info@namiscia.org
Website
11:00 am to 1:00 pm
Mahaska Drug
Christmas Eve Santa Sing Along
Oskaloosa, IADecember 24, 2025
11:00 am · 1:00 pm
10:00 am to 11:00 am
Environmental Learning Center
Reindeer Facts & Fun!
Oskaloosa, IADecember 29, 2025
10:00 am · 11:00 am
Join us for a fun Reindeer program! Participants will learn all about these amazing animals—what they eat, where they live, and how they survive in the cold. We’ll explore fun reindeer facts and get into the winter spirit together. Perfect for young and old nature lovers!
Sign up online using this link by noon on Dec. 28th: Reindeer Facts & Fun! - Caldwell Park, Mahaska County, IA - MyCountyPark.com
5:00 pm to 7:00 pm
Rosso & Wine
Wine Tasting at Rosso & Wine
Penn Central Mall - 200 High Avenue WestOskaloosa, IA
Map to Event
December 30, 2025
5:00 pm · 7:00 pm
Enjoy some Wine Tasting at Rosso & Wine.
For More Information(641) 676-8466
6:30 pm
The Eagles
Bingo @the Eagles
215 High Ave EastOskaloosa, IA
Map to Event
December 30, 2025
6:30 pm
Bingo at the Eagles starting at 6:30 PM
8:00 pm to 12:00 am
The Eagles
M&M @The Eagles
Oskaloosa, IADecember 31, 2025
8:00 pm · 12:00 am







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