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Labor day weekend Events and Things to do in Winchester, VA

Lucketts Spring Market
Fri, May 15, 8:30 AM
Berryville · Clarke County Ruritan Fairgrounds
Lucketts Spring Market
Fri, May 15, 8:30 AM
Berryville · Clarke County Ruritan Fairgrounds
The Super 70's Rock Show featuring Super Trans AM and The Darby Brothers
Sat, Sep 5, 6:00 PM
Leesburg · Tarara Winery
The Super 70's Rock Show featuring Super Trans AM and The Darby Brothers
Sat, Sep 5, 6:00 PM
Leesburg · Tarara Winery
Labor Day with Uncle Sam & the Eagle
Mon, Sep 7, 12:00 PM
Tysons · 7581 Colshire Dr
Labor Day with Uncle Sam & the Eagle
Mon, Sep 7, 12:00 PM
Tysons · 7581 Colshire Dr
The 22nd Annual Watermelon Pickers' Fest
Thu, Sep 10, 9:00 AM
Berryville · Clarke County Ruritan Fairgrounds
The 22nd Annual Watermelon Pickers' Fest
Thu, Sep 10, 9:00 AM
Berryville · Clarke County Ruritan Fairgrounds
DC Labor Day Weekend Pier Pressure Yacht Party Cruise
Sun, Sep 6, 3:30 PM
Washington · Spirit of Washington DC by Hornblower
DC Labor Day Weekend Pier Pressure Yacht Party Cruise
Sun, Sep 6, 3:30 PM
Washington · Spirit of Washington DC by Hornblower
Mother’s Day Lantern Walk: Roots, Blooms, and Seeds
Sat, May 9, 5:30 PM
Barnesville · 17500 Conoy Rd
Mother’s Day Lantern Walk: Roots, Blooms, and Seeds
Sat, May 9, 5:30 PM
Barnesville · 17500 Conoy Rd
Mother's Day Brunch at Patti’s Place
Sun, May 10, 11:00 AM + 7 more
Winchester · Patti's Place
Mother's Day Brunch at Patti’s Place
Sun, May 10, 11:00 AM + 7 more
Winchester · Patti's Place
Hagerstown Mother’s Day Craft & Vendor Market
Fri, May 8, 11:00 AM
Hagerstown · Valley Mall
Hagerstown Mother’s Day Craft & Vendor Market
Fri, May 8, 11:00 AM
Hagerstown · Valley Mall
2026 Hunt Country Stable Tour
Upperville · Trinity Episcopal Church
2026 Hunt Country Stable Tour
Upperville · Trinity Episcopal Church
Labor Day Beach Bar Crawl
Sat, Sep 5, 3:00 PM
Arlington · Clarendon's Top Bars
Labor Day Beach Bar Crawl
Sat, Sep 5, 3:00 PM
Arlington · Clarendon's Top Bars
32nd Annual James E. Childs Scholarship Golf Tournament
Mon, Jun 1, 9:00 AM
Front Royal · Blue Ridge Shadows Golf Club
32nd Annual James E. Childs Scholarship Golf Tournament
Mon, Jun 1, 9:00 AM
Front Royal · Blue Ridge Shadows Golf Club
Stifler’s Mom - The Ultimate ‘90s Experience
Fri, Jul 3, 6:00 PM
Leesburg · Tarara Winery
Stifler’s Mom - The Ultimate ‘90s Experience
Fri, Jul 3, 6:00 PM
Leesburg · Tarara Winery
Labor Day Beach Bar Crawl
Sat, Sep 5, 3:00 PM
Arlington · Clarendon Top Bars
Labor Day Beach Bar Crawl
Sat, Sep 5, 3:00 PM
Arlington · Clarendon Top Bars
Delta Spur - Country Music Favorites
Sat, Jun 20, 6:00 PM
Leesburg · Tarara Winery
Delta Spur - Country Music Favorites
Sat, Jun 20, 6:00 PM
Leesburg · Tarara Winery
Sleepy Creek Spring Fling Fest
Wed, May 6, 12:00 PM
Berkeley Springs · Joshua Lane
Sleepy Creek Spring Fling Fest
Wed, May 6, 12:00 PM
Berkeley Springs · Joshua Lane
2nd Annual Cider & Seltzer Festival at Bear Chase!
Sat, Jun 13, 11:00 AM
Bluemont · Bear Chase Brewing Company
2nd Annual Cider & Seltzer Festival at Bear Chase!
Sat, Jun 13, 11:00 AM
Bluemont · Bear Chase Brewing Company
CHEDDAR ROCK 2026
Fri, Jun 19, 12:00 PM
Middletown · Middletown
CHEDDAR ROCK 2026
Fri, Jun 19, 12:00 PM
Middletown · Middletown
Memorial Day Weekend Rooftop Beach Bash
Sat, May 23, 3:00 PM
Arlington · Clarendon Ballroom
Memorial Day Weekend Rooftop Beach Bash
Sat, May 23, 3:00 PM
Arlington · Clarendon Ballroom
Frederick Mother’s Day Craft & Vendor Market
Friday at 11:00 AM
Frederick · Francis Scott Key Mall
Frederick Mother’s Day Craft & Vendor Market
Friday at 11:00 AM
Frederick · Francis Scott Key Mall
24th Annual Tour de Skyline
Fri, Sep 11, 9:00 AM
Front Royal · Dickey Ridge Visitor Center
24th Annual Tour de Skyline
Fri, Sep 11, 9:00 AM
Front Royal · Dickey Ridge Visitor Center

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