What's Up Weston
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All Events & Festivals
Events Calendar
Discover wine tastings, festivals, and cultural experiences in our historic town
Thu
Food & Drink
BOGO
Thursday Double Take
Thursday, September 24, 2026
2:00 PM - 6:00 PM
Weston Wine Company
Thu
Fun & Games
$5.00
Dinner and Bingo Fundraiser
Thursday, September 24, 2026
10:00 PM
Masonic Lodge
Thu
Food & Drink
Free
Sunset Sips at the Vineyard at Pirtle Winery
Friday, September 25, 2026
12:00 AM - 2:00 AM
The Vineyards @ Pirtle Winery
Thu
Fun & Games
Free
Music Bingo
Friday, September 25, 2026
2:00 AM
Beers To You Saloon
Fri
Food & Drink
$12 - $18
Friday Sip Trip
Friday, September 25, 2026
2:00 PM - 7:00 PM
Weston Wine Company
Fri
Music
Free
Live Music at Riverwood Winery!
September 25 - September 26, 2026
10:00 PM - 1:00 AM
Riverwood Winery
Fri
Family
Free
1st Missouri Paw Paw Festival
September 25 - September 26, 2026
11:00 PM - 4:59 AM
Weston Brewing Co
Fri
Music
Free
Live Music at The Whiskey Snug
September 25 - September 26, 2026
11:00 PM - 1:00 AM
The Whiskey Snug
Fri
Music
Free
Live Music at Walnut Creek
September 25 - September 26, 2026
6:00 PM to 9:00 PM
Walnut Creek of Weston
Fri
Music
$5.00
Live Music at O'Malley's
Saturday, September 26, 2026
1:00 AM - 4:59 AM
O'Malley's Pub
Fri
Family
$5
Outdoor Movie Night
Saturday, September 26, 2026
1:00 AM
O'Malley's Pub
Fri
Music
Free
Karaoke at Beers to You
Saturday, September 26, 2026
2:00 AM - 6:00 AM
Beers To You Saloon
Sat
Food & Drink
Free
Biscuits and Gravy Fundraiser Breakfast
Saturday, September 26, 2026
7-10AM
Masonic Lodge of Weston
Sat
Music
Free
Live Music at The Vineyards at Pirtle
Saturday, September 26, 2026
1:00PM - 4:00PM and 5:30PM - 8:30PM
The Vineyards @ Pirtle Winery
Sat
Music
Free
Live Music at The Vineyards at Pirtle
Saturday, September 26, 2026
1:00PM - 4:00PM and 5:30PM - 8:30PM
The Vineyards @ Pirtle Winery
Sat
Fun & Games
$17.99
Pumpkin Fest at the Orchard
Saturday, September 26, 2026
2:00 PM - 10:00 PM
Historic Weston Orchard & Vineyard
Sat
Community
Free
Outdoor Yoga at the Orchard
Saturday, September 26, 2026
3:00 PM - 4:00 PM
Historic Weston Orchard & Vineyard
Sat
Family
Free
1st Missouri Paw Paw Festival
September 26 - September 27, 2026
4:30 PM - 4:59 AM
Weston Brewing Co
Sat
Fun & Games
$45
Sat
Music
Free
Live Music at Coal House Saloon
Saturday, September 26, 2026
1:00 PM - 4:00 PM
The Coal House Saloon
Sat
Music
Free
Live Music at Riverwood!
September 26 - September 27, 2026
6:00 PM - 1:00 AM
Riverwood Winery
Sat
Music
Free
Live Music at Holladay Distillery!
Saturday, September 26, 2026
6:00 PM - 9:00 PM
Holladay Distillery
Sat
Music
Free
Live Music at Walnut Creek
Saturday, September 26, 2026
3:00 PM to 6:00 PM
Walnut Creek of Weston
Sat
Community
Free
Weston Moonshiners Car Cruise!
September 26 - September 27, 2026
10:00 PM - 2:00 AM
Weston Moonshiners Car Club
Sat
Music
$5.00
Live Music at O'Malley's
Sunday, September 27, 2026
1:00 AM - 4:59 AM
O'Malley's Pub
Sun
Food & Drink
$22
Sun
Music
Free
Live Music at the Holladay Distillery
Sunday, September 27, 2026
5:00 PM - 8:00 PM
Holladay Distillery
Sun
Culture
Free
Summer Speaker Series
Sunday, September 27, 2026
5:30 PM - 7:00 PM
Black Ancestors Awareness Campaign
Sun
Music
Free
Live Music at Riverwood Winery!
Sunday, September 27, 2026
6:00 PM - 9:00 PM
Riverwood Winery
Sun
Music
Free
Bob Reeder Live at O'Malley's
September 27 - September 28, 2026
9:00 PM - 1:00 AM
O'Malley's Pub