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Upperville
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Popular Events in Upperville, VA
Nov
22
A Trail Through Time
Nov 22, 2026 11:00 AM - 01:00 PM
Sky Meadows State Park
Free
Nov
14
Winter Tree Identification Workshop: Botany and Bloom Series
Nov 14, 2026 10:00 AM - 02:00 PM
Sky Meadows State Park
Free
Nov
14
Autumn Impressions: Nature-Inspired Clay Ornament Craft Session
Nov 14, 2026 12:00 PM - 02:00 PM
Sky Meadows State Park
Free
Nov
8
3rd Annual Great Meadow Veterans Cup: Polo with Purpose
Nov 08, 2026 11:00 AM - 04:00 PM
Great Meadow
0.00 USD - 1000.00 USD
Nov
21
Fall Watercolor Workshop and Brunch
Nov 21, 2026 10:30 AM - 01:30 PM
6809 Airlie Road
120.82 USD
Nov
27
Black Friday Turkey Trek
Nov 27, 2026 11:00 AM - 01:00 PM
Sky Meadows State Park
Free
Dec
5
Winter Tree-mendous Hike
Dec 05, 2026 10:00 AM - 11:00 AM
Sky Meadows State Park
Free
Nov
22
Standup Comedy at Old Bust Head (Warrenton, VA)
Nov 22, 2026 06:30 PM - 08:00 PM
Old Bust Head Brewing Company
12.51 USD
Nov
14
Warrenton Relief Society Service Activity
Nov 14, 2026 10:00 AM - 12:00 PM
The Church of Jesus Christ of Latter-day Saints
Free
Nov
15
Fall Color Quest
Nov 15, 2026 11:00 AM - 12:00 PM
Sky Meadows State Park
Free
Upperville, VA · Latest Local
Events
Upcoming
Weekend
New
Oct
4
Investment in Wealth & Luxury
Oct 04, 2026 12:00 PM - 03:00 PM
The Hunt Estates LLC
59.99 USD
Aug
7
Playing in the Vines
Aug 07, 2026 02:00 PM - 05:00 PM
1500 Crenshaw Road
Aug
14
10th Annual CrabFest
Aug 14, 2026 03:00 PM - 06:00 PM
Slater Run Vineyards
Jul
11
Lowcounty Boil with T. T. Wall's
Jul 11, 2026 03:00 PM - 06:00 PM
1500 Crenshaw Road
May
23
2026 Hunt Country Stable Tour
May 23, 2026 06:00 AM - May 24, 2026 12:00 PM
Trinity Episcopal Church
USD 45 to 165
Apr
23
Historic Garden Week 2026: Little Oak Spring
Apr 23, 2026 05:00 AM - Apr 24, 2026 12:00 PM
Oak Spring Garden Foundation
USD 79
Jan
18
Uncork Your Dreams – A Vision Workshop with DeeAnn Jeremiah at Slater Run
Jan 18, 2026 01:00 PM - 02:00 PM
Slater Run Vineyards
63.74 USD
Dec
7
The Very Best Time of Year
Dec 07, 2025 10:00 AM - 11:00 AM
Trinity Episcopal Church
Nov
20
A Toast to Tradition: The Stirrup Cup Release
Nov 20, 2025 04:00 AM
1500 Crenshaw Road
Nov
16
Wine + Nine: Six Sips. Nine Types. One Eye-Opening Afternoon at Slater Run
Nov 16, 2025 01:00 PM - 02:00 PM
Slater Run Vineyards
63.74 USD
Jun
28
A Tour of the Garden and Gallery at Oak Spring Garden - Day 2
Jun 28, 2025 09:00 AM - 04:00 PM
Oak Spring Garden Foundation - Formal Garden
81.88 USD
Jun
4
Art Under the Oaks
Jun 04, 2025 02:00 PM - 07:00 PM
Upperville Horse Show
Jun
7
Wall of Honor Induction Ceremony
Jun 07, 2025 04:00 PM
8300 John S Mosby Hwy
Jun
27
A Tour of the Garden and Gallery at Oak Spring Garden - Day 1
Jun 27, 2025 09:00 AM - 04:00 PM
Oak Spring Garden Foundation - Formal Garden
81.88 USD
Jun
12
Flower House Detroit
Jun 12, 2025 01:00 PM - 03:00 PM
Oak Spring Garden Foundation | The Granary
Free
Jun
4
Art Under the Oaks
Jun 04, 2025 07:00 AM - 12:00 PM
8300 John S Mosby Hwy
Jun
6
3rd Annual Feast in the Field
Jun 06, 2025 05:30 PM - 08:30 PM
Oak Spring Garden Foundation - Walled Garden
225.00 USD
May
24
2025 Hunt Country Stable Tour, Featuring 8 New Farms!
May 24, 2025 10:00 AM - May 25, 2025 04:00 PM
Trinity Episcopal Church
45.00 USD - 250.00 USD
May
17
Paint Out: In the Walled Garden - Independent Work Session for Artists
May 17, 2025 08:00 AM - 12:00 PM
Oak Spring Garden Foundation
15.00 USD
May
17
An Exploration of Landscape and History
May 17, 2025 09:00 AM - 04:30 PM
Oak Spring Garden Foundation
50.00 USD
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