All of Virginia’s wineries offer stunning scenery and world-class wine, but a few wineries go above and beyond, providing unique experiences that make the visit unforgettable. From polo matches and kayaking expeditions to distinct wine tasting pairings and horseback rides, these eleven wineries provide exciting entertainment to turn your typical vineyard visit into a fun-filled Virginia adventure.
Paddle Your Glass Off to Chatham Vineyards on Virginia’s Eastern Shore
Photo Credit: Sam Dean, IG account: @sdeanphotos
The beautiful Eastern Shore winery, Chatham Vineyards, has teamed up with Southeast Expeditions to offer a relaxing 45 minute paddle tour through Church Creek on your way from the local Wharf of Bayford to Chatham Vineyards. Guides identify local wildlife and aquaculture along the way and show you around the historic property once ashore. After your complimentary wine tasting, there’s always time to sit outside with a glass of wine and a cheese tray to enjoy the vineyard before paddling back. The cost is $89 per paddler and covers the guide, gear, boat, winery experience, and a complimentary bottle of Church Creek wine for every two paddlers.
Sample Fresh Seafood at The Dog & Oyster Vineyard
Is there really anything better than enjoying a glass of chilled white wine with a sampling of delicious Virginia oysters? Head to the Dog & Oyster Vineyard in Irvington to savor this incredible pairing, with Chesapeake Bay oysters served at Slurp, the winery’s on-site oyster restaurant and bar. With the Bay less than a mile from the vineyard, you’re guaranteed to get only the freshest oysters at this waterfront wine destination.
Catch Bridgerton Vibes at Northern Virginia’s Greenhill Winery
Greenhill Winery in Loudoun County offers old-school carriage rides through the vineyard, allowing visitors to pretend they’re on the set of Netflix’s Bridgerton while sipping a glass of sparkling Blanc de Blanc. In addition to romantic carriage rides, the winery has their own polo team, a nod to the winery’s location in Virginia’s Horse Country; contact the vineyard for information on upcoming polo matches.
Find Your Zen at Veritas Vineyards
Veritas Vineyards near Charlottesville offers one-, three-, and four-day yoga retreats, with a comprehensive program of hiking, yoga, food, and wine experiences to delight your senses. The schedule includes educational vineyard tours, hiking the Appalachian Trail, cooking classes, and of course—lots of yoga in the Garden House. The days end with a social cocktail hour featuring Veritas wines paired with light fare. The winery also hosts Starry Nights events on select summer evenings, with outdoor live music performances, Veritas wines, buffet-style food offerings by reservation, and an unforgettable evening under the stars. Check the winery events page for updates on scheduled Starry Nights events.
Explore Charlottesville Wine Country by Horseback
Photo Credit: Carlita Pitts IG: @iamthelita
Explore Central Virginia’s wine country by horseback with Indian Summer Guide Services. This guided riding experience is available at several wineries in the Charlottesville and Albemarle County area, including King Family Vineyards, Veritas Vineyard, Keswick Vineyards, Glass House Winery, and more. These five-star private, guided horseback rides through the vines allow you to learn about the grapes and the vineyard’s production process while getting an up-close look at the Virginia terroir that results in world-class wines.
Bike to Upper Shirley Vineyards Along the Virginia Capital Trail
Photo Credit: Big Orange Frame
Based out of Richmond, Basket & Bike teamed up with the gorgeous Upper Shirley Vineyards for its Signature Ride, returning in Mid-March 2021. Departing from Upper Shirley Vineyards, you’ll enjoy a leisurely, 14-mile guided bicycle tour along the Virginia Capital Trail where you’ll learn about Virginia’s history and the picturesque landscape viewed from the Capital Trail. Priority bikes are outfitted with Nantucket Bike Baskets, or riders have the choice to opt for RVA on Wheels Pedego electric bikes for an easier ride. The tour includes a glass of wine and lunch at Upper Shirley Vineyards, and $5 of the tour fee goes towards supporting one of the rotating conservation partners (Capital Trees, James River Association, VCU Rice Rivers Center, BridgePark RVA), allowing you to support local nonprofits while also enjoying the Great Outdoors, Virginia history, and some marvelous wine.
Attend a Proper Polo Match at King Family Vineyards
Photo Credit: Matthew Brown
Beginning in May, King Family Vineyards hosts weekly polo matches on Sundays, where visitors can set up a socially-distanced family picnic and sip on King Family wines with a stunning backdrop of the Blue Ridge Mountains. These events are free and open to the public, but are weather dependent; check the website or their Facebook page for current updates on the Roseland polo matches at King Family Vineyards.
Escape to the Tropics at Glass House Winery
Photo Credit: Carlita Pitts IG: @iamthelita
Glass House Winery has built a stunning tropical conservatory attached to its tasting room, filled with exotic plants surrounding tables and walkways. You’ll feel as if you’re sipping your wine on a far-away island rather than in the heart of Central Virginia’s wine country. Don’t miss out on pairing your wines with the vineyard’s decadent chocolates, made in-house by their very own chocolatier, which come in flavors like raspberry champagne, salted peanut butter, red wine cream, and cherry chilli.
Tee Off at Little Washington Winery
About 60 miles west of Washington, D.C. in the foothills of Shenandoah National Park, Little Washington Winery & Brewery combines scenic views with outdoor sports on their 18-hole par 60 Jenkins Mountain Disc Golf Course. The course spans 55 acres with the Blue Ridge Mountains in the background, and is open to the public year-round at no extra cost (just bring your own discs!). Start your game at Hole #1, located right at the winery/brewery entrance, but stop into the Pro Shop first to stock up on snacks, drinks, and accessories for your game. As you play the course, you’ll come across the Skyline Vineyard, where you can take a break and grab some food. Depending on the day, you may even catch some live music! Finish up hole #18 back at the brewery/winery entrance, toasting the winner with a glass of Little Washington wine or beer.
Dig Into Wine & Pie Pairings at 8 Chains North Winery
Photo Credit: Emily Powers
8 Chains North Winery and Mom’s Apple Pie Company, a Loudoun bakery popular with the locals, are owned by a brother and sister duo. After solidly establishing the winery and bakery, the two decided to team up for special wine and pie pairings. Want more sweet sugary goodness during your visit to 8 Chains North? The winery also carries chocolates from local chocolatier and restaurant, The Conche, which can be paired with your tasting for only $5 more.
Soothe Your Senses at Purple Wolf Vineyard
Photo Credit: Chad Williams; IG account: @echadwilliams
At Purple Wolf Vineyard, the wine isn’t the only relaxing aspect of your visit; the tasting room is actually part of White Oak Lavender Farm, located outside of Harrisonburg. Before visiting the tasting room, take some time to walk through the Discovery Area, an interactive garden space with a petting area, life-size checkerboard, duck pond, labyrinth, oil distillery, drying barn, and of course, lavender gardens. Visitors can pick their own lavender when in season, as well as purchase a wide variety of lavender products from the gift shop, such as lavender body products, teas, culinary lavender, and even lavender ice cream. If you’re interested in learning more about the lavender growing and harvesting process, take the farm’s self-guided audio tour, which for only $9 covers your entrance to the Discovery Area and picking 20 stems of lavender (when in bloom).
Once you’ve toured the property, finish up in the tasting room, sampling up to 12 unique wines in mini tastings, flights, or seasonal wine treats like slushies. Your lavender experience doesn’t end at the winery doors, though. Some of the wines are infused with lavender, a surprisingly refreshing twist to the classic glass of Virginia vino.