Hey Winstigators,
Last summer, I wrote about spending a Saturday evening watching polo at Great Meadow in The Plains. So when my family and I made plans to meet some friends for Twilight Polo this past Saturday, I knew exactly where we were going…or at least I thought I did.
We packed everyone and everything into the car, drove to Great Meadow, saw the signs out front announcing “Polo Today” and figured we were in the right spot. Unfortunately, our friends were nowhere to be found.
After circling the parking lot and begging for the extra bar of cell phone reception necessary to make a call, we discovered that they were waiting for us at Twilight Polo in Middleburg. We, meanwhile, were sitting at Great Meadow in The Plains, approximately 20 minutes away, attending an entirely different Saturday evening polo event. In my defense, this is more confusing than it sounds.
For years, Twilight Polo was closely associated with Great Meadow, where the Saturday-night series had been held since the 1990s. Great Meadow still hosts polo on Saturday evenings, but its current event is the Great Meadow Polo Summer Series. The event officially called Twilight Polo is now held at its own facility on Charisma Lane, just outside downtown Middleburg. They are two separate events at two separate venues, even though both offer evening polo in Virginia horse country and are close enough together to create exactly the kind of situation in which we found ourselves.
Once we realized our mistake, we headed over to Middleburg. It wasn’t our smoothest family outing, but we were still going to see polo. We just needed to find the correct polo, and thankfully, Twilight Polo was worth the detour.
The event takes place in an intimate arena surrounded by the rolling countryside that makes the Middleburg area feel like Middleburg. The setting is beautiful, but the atmosphere is much more relaxed than you might expect from something involving polo, horses and Virginia hunt country.
You do not need to know the rules, own an elaborate hat or arrive carrying a silver tray of cucumber sandwiches…although if you have those things, great. You can bring chairs or a blanket, pack your own food and drinks, find a place to settle in and enjoy the evening.
Our friends had reserved a tailgating spot right beside the arena, which put us only a few steps away from the wall. Whenever something interesting started happening, we could walk down, lean over and watch the match from close range. It gave the evening the feeling of a relaxed backyard gathering, except there were polo players and horses thundering past a few feet away.
Admission to Twilight Polo is free, and the event is genuinely family-friendly. There were kids everywhere playing pickup soccer, throwing footballs and running around, many of them completely oblivious to the matches happening beside them. Parents could watch the action and talk with friends without expecting the children to sit quietly and pretend to understand the finer points of polo. That is probably the event’s biggest strength: the matches give everyone a reason to be there, but the real appeal is spending time with friends and family, packing some food and enjoying a summer evening outside. It works equally well as a family outing, a date night or an easy night out with friends.
My son loved it. Along with the general freedom to run around, he was thrilled by the chance to give the players high-fives and pet the horses between matches. At the end of the evening, the kids were invited onto the field to try hitting balls with polo mallets before finishing the night with a few games of tug-of-war. Those small interactions made the experience feel much more welcoming than people might expect from polo. The players were accessible to the crowd, the horses were close enough for the kids to see and touch and the event made families feel like part of the evening rather than an afterthought.
The Middleburg event also has a slightly different feel from the polo at Great Meadow. Great Meadow is a much larger venue, and the wide-open stadium creates more of a traditional tailgating atmosphere. Twilight Polo feels smaller and more intimate, with spectators gathered closely around the arena and more opportunities to interact with the players and horses.
Neither approach is necessarily better, and both can make for a fun Saturday night. You simply need to know which one your friends are attending before you leave the house.
Despite our geographically challenged start, we had a great evening. Twilight Polo manages to feel distinctly Middleburg without becoming stuffy or inaccessible. It is beautiful, entertaining, welcoming to families and different from the usual dinner, brewery or live-music routine. The fact that admission is free makes it especially easy to recommend, although I would strongly suggest double-checking the address before you go.
Twilight Polo is located at 37636 Charisma Lane in Middleburg. Great Meadow Polo is located at 5089 Old Tavern Road in The Plains. Both involve horses, mallets and Saturday evenings. Only one of them will have the friends you arranged to meet.
National Hot Dog Day!
No, it’s not Winchester specific…but to those who celebrate, today is National Hot Dog Day! Whether you prefer yours grilled, boiled, covered in chili or buried beneath an irresponsible amount of toppings, this is your day to eat one for lunch and another for dinner, guilt free. Please observe this important national occasion responsibly.
If you want a quick guide on how you can celebrate, here’s some more information.
Homes Of The Week!
Events and Happenings in Winchester and the surrounding territories:
Friday, July 17th
Old Town Winchester Walking Mall, Winchester - Monty Python Pub Crawl, July 17, 6pm - 9pm
James Charles Winery & Vineyard, Winchester - Pre-Release Club Tasting, July 17, 7pm - 9pm
Main Street Martinsburg, Martinsburg - Fridays @ Five - Luke Demers Trio, July 17, 5pm
AllEvents, - Little River Band,
Bistro The Porch, The Plains - Bistro @ The Porch - 2026 MurLarkey Cocktail Dinner, July 17, 7pm - 8:30pm
Bridgeforth Field, Winchester - Winchester Royals vs Strasburg Express, July 17, 7pm - 10pm
The Half Note, Winchester - Robbie Limon Live at the Half Note Lounge, July 17, 8pm - 10pm
Pklplex of Winchester Virginia, Winchester - Battle of the Paddles, July 17, 4am
West Oaks Farm Market, Winchester - Farm Concert: Chad Laughlin Band, July 17, 7pm - 10pm
Warren Heritage Society Inc., Front Royal - Haunted Front Royal Ghost Tours, July 3 - July 17
Salamander Middleburg, Middleburg - Mixology Class: Tequila Cocktails, July 17, 4:45pm - 6:30pm
Cams Quick Lube, Romney - Christmas in July - Bike Night & Drive-in Movie Night, July 17, 6pm
Dirt Farm Brewing, Bluemont - Lobster Roll Weekends at Dirt Farm, July 3 - July 17
Saturday, July 18th
The YDC, Winchester - The All-American Pig & Pour, July 18, 3pm - 9pm
Hollywood Casino, Charles Town - Rick Springfield at Hollywood Casino at Charles Town Races,
Washington County Ag Expo, Fairplay - Washington County Ag Expo Kick-Off, July 18, 12pm - 2pm
Cool Spring Battlefield, Berryville - 161st Anniversary Commemoration of Battle of Cool Spring, July 18, 9:30am
Winchester Book Gallery, Winchester - Author Event: Nicole Hanlin – Social Beyond Media, July 18, 11am - 1pm
Jim Barnett Park, Winchester - Fun in the Sun at Jim Barnett Park Pool, July 18, 12pm - 5pm
Fireman's Field, Purcellville - Purcellville Wine and Food Festival, July 18, 2pm - 8pm
Tally Ho Theater, Leesburg - Magic City Hippies at Tally Ho,
Tarara Winery, Leesburg - Turnstiles - The Ultimate Tribute to the Music of Billy Joel, July 18, 6pm - 9:30pm
Summit Point Motorsports Park, Summit Point - Mach V Summer Trackcross Rounds 3 & 4, July 18, 7am - 5pm
Museum of the Shenandoah Valley, Winchester - Antique & Modified Car Show, July 18, 10am
Bright Box Theater, Winchester - The Riff Rampage Tour! @Bright Box, July 18, 7pm
Cousins Maine Lobster - Virginia, Delaplane - 🦞 Cousins Maine Lobster at Barrel Oak Winery and Brewery ✨, July 18, 2pm - 7pm
The Half Note, Winchester - Justin Lees Live at the Half Note Lounge, July 18, 8pm - 10pm
Brunswick, Maryland, Brunswick - One Day Rafting Retreat in Harpers Ferry with VSDC, July 18, 10am
John H. Enders Fire Company, Berryville - 76th Annual Firefighters Chicken BBQ Dinner & Online Silent Auction, July 18, 1pm - 7pm
Winchester Little Theater, - James and the Giant Peach Jr. - WLT For Kids at Winchester Little Theatre Inc- Multiple Dates and Times Available!
Sunday, July 19th
Museum of the Shenandoah Valley, Winchester - Presentation: Sarah Strother’s Story, July 19, 2pm - 3pm
The Great Meadow Foundation, The Plains - Teodoro Reyes, Frank Reyes, El Varon de la bachata, Zacarias Ferreira, Los Toros Band, Jennifer Ventura, Monchy in The Plains, July 19, 12pm - 2pm
Odie And The Country Band, Sharpsburg - Taste of Washington County at The Washington County Ag Expo live music by Odie and The Country Band, July 19, 1pm
Segra Field, Leesburg, - Loudouns 2026 World Cup Final Watch Party,
Abbie Martin Art, Purcellville - Christmas in July @ 868 Estate Vineyards, July 19, 1pm - 3:30pm
Connected Communities, Winchester - Community Closet by Connected Communities, June 14 - July 19
Breaux Vineyards, Purcellville - Live Music with Ryan Sill, July 19, 2pm - 5pm
K9ology Training & Behavior, Sperryville - Rescue me! A look at rescue dogs!, July 19, 6:30pm
Archwood Green Barns Farmer's Market, The Plains - Archwood Green Barns Main Farmers' Market Season, May 24 - July 19
Point of Rocks Railroad Station, Point Of Rocks - The Ice Cream Sunday Ride, July 19, 8am
Dirt Farm Brewing, Bluemont - Summer Sundays Live Music feat. Personal Moose, July 19, 1pm - 4pm
West Oaks Farm Market, Winchester - Murphy's Bluegrass Bandits Live!, July 19, 1pm - 4pm
Black Draft Distillery, Martinsburg - Textured Tides Paint & Sip, July 19, 1pm - 3pm
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Have fun out there!
