Hey Winstigators,
I was down in Arlington/DC this past weekend and it didn’t take long to remember why I like it here so much. Everything down there just feels…louder. More traffic, more people, more everything. It’s fun in short bursts, but after a couple days, I found myself missing how easy Winchester is.
Pulled back into town and it just felt calmer. No chaos, no fighting for space, just a normal, easy pace that you don’t really notice until you leave it for a bit. Winchester’s not perfect, but it’s got a rhythm that’s hard to beat once you get used to it.
Anyway, there’s a lot to do this weekend, especially with Easter coming up!
Homes Of The Week!
Events and Happenings in Winchester and the surrounding territories:
Friday, March 27th
George Washington Hotel, Winchester - VA250: Cocktails and History, March 27, 6pm - 7:30pm
Charles Town, WV, Charles Town - Cheap Trick: All Washed Up Tour, March 27, 8pm
Murphy Beverage Company, Winchester - Wine tasting at Murphy Beverage Company, March 27, 5:30pm - 7pm
Bavarian Inn Resort & Brewing Company, Shepherdstown - 🍷 The 25th Annual Wine Dinner: A Napa Valley Celebration for Rotary Reads, March 27, 6:30pm
James Charles Winery & Vineyard, Winchester - Trivia Night, March 27, 7pm - 10pm
Theatre Shenandoah, Edinburg - The Sound of Music, March 20 - March 27
George Washington Hotel, Winchester - VA250: Cocktails and History, March 27, 6pm - 7:30pm
Backseat Events, Winchester - 🎶 The Travelin’ McCourys — Young Guns Tour 2026 🎶, March 27, 8pm
Front Royal Golf Club, Front Royal - Front Royal Little League Golf Tournament, March 27, 9am - 3pm
Paladin Bar & Grill, Stephens City - Bearded Harmony Live @ Paladin Bar & Grill, March 27, 7pm - 10pm
Salamander Middleburg, Middleburg - Mixology Class: Cherry Blossom Cocktails, March 27, 4:45pm - 6pm
Box Office Brewery, Strasburg - Shockwave @BoxOffice, March 27, 7pm - 10pm
Piccadilly's Public House and Restaurant, Winchester - Local Boy Timmy @ Piccadilly's, March 27, 7:30pm - 11:30pm
Saturday, March 28th
Hollywood Casino at Charles Town Races, Charles Town - Jay Leno And Arsenio Hall, March 28, 7pm
Leesburg Animal Park, Leesburg - Easter Egg Hunt, March 28, 11am - 3pm
Breaux Vineyards, Purcellville - 2026 Cherry Blossom Festival, March 28, 11am - 6pm
The War Memorial Building, Shepherdstown - Shepherdstown Easter Market, March 28, 10am - 3pm
Bright Box Theater, Winchester - The Darkside Experience: A Tribute to Pink Floyd, March 28, 8pm
North Mountain Vineyard & Winery, Maurertown - 🌶️ Annual Chili Cook-Off at North Mountain Vineyard & Winery 🌶️, March 28, 11am
Heritage Hall Banquet and Event Center, Inwood - RESCUE ME WV PRESENTS: SPORTSMAN’S BARK BASH, March 28, 12pm - 6pm
Dormition of the Virgin Mary Greek Orthodox Church, Winchester - Easter Bake Sale and Greek Takeout, March 28, 11am - 4pm
The Winchester Book Gallery, Winchester - Author Event: Mari-Jo Qualey - Soul Evidence, March 28, 2pm - 4pm
The Yellow School House, Winchester - The Baby Buzz, March 28, 9:30am - 2:30pm
Upstairs at Smoketown, Brunswick - Multi-Band Benefit Concert @ UpstairsAtSmoketown - Mack Berry Band, March 28, 4pm
Summit Point Motorsports Park, Summit Point - Summit Point Test Drive #1 - HPDE a la Carte [Shenandoah 3.28.26], March 28, 7:30am - 5:30pm
Crooked Run Fermentation, Sterling - Country Nite @ Crooked Run Fermentation in Sterling, March 28, 7pm - 11pm
Winchester Country Club, Winchester - Lincoln Reagan Dinner, March 28, 6pm - 10pm
Nibblins, Winchester - Easter Breads, March 28, 4:30pm
The Garage on King, Martinsburg - Mission Road, March 28, 8pm - 11pm
Sunday, March 29th
West Oaks Farm Market, Winchester - West Oaks 7th Annual Adult Egg Hunt, March 29, 12pm - 3pm
Sherando Park, Stephens City - Kite Flying Festival, March 29, 1pm - 4pm
Stitch Needlepoint, Middleburg - Learn to Stitch! 2 PM
Bright Box Theater, Winchester - Lovesong - The Cure Tribute w/ First Wave, March 29, 6pm
Middletown, VA, United States, Middletown - The Marshall Tucker Band in Middletown, March 29, 7pm - 9pm
Salamander Middleburg, Middleburg - Easter Bunny Experience, March 29, 1pm - 4pm
Tarbender's Lounge, Leesburg - March's Stand-Up Comedy Brunch At Tarbender’s Lounge, March 29, 1pm - 2:30pm
Red Gate Farm, LLC, Bluemont - Dressage Show (VADA/NOVA), March 29, 9am - 2pm
C&O Canal Towpath, Sharpsburg - Wildflower Walk at the C&O Canal Towpath near Shepherdstown | Mobility-friendly, March 29, 1pm - 3pm
Summit Point Motorsports Park, Summit Point - Get On Track/Trackcross Practice/Skidpad #1 [Shenandoah 3.29.26], March 29, 7:30am - 6pm
Bear Chase Brewing Company, Bluemont - Nesting Bowl Workshop, March 29, 12pm - 2pm
Deliteful Dairy, Williamsport - Deliteful Dairy's Easter Egg Hunt, March 29, 2pm - 3:30pm
Bishops Events, Leesburg - 2026 Doggy Dash 5k/10k, March 29, 8:45am
Breaux Vineyards, Purcellville - Live Music with Shane Gamble, March 29, 2pm - 5pm
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Have fun out there!
