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

Paddle Your Glass Off Kayak Tour

Photo Credit: Sam Dean, @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 & Wine at The Hope & Glory Inn's Micro-Vineyard


Is there really anything better than enjoying a glass of chilled white wine with a sampling of delicious Virginia oysters? Head to the Hope & Glory Inn in Irvington to savor this incredible pairing, with Chesapeake Bay oysters from local watermen served with wines from this boutique inn's micro-vineyard, the Dog & Oyster. With the Bay less than a mile from the inn, you’re guaranteed to get only the freshest oysters at this waterfront wine destination. 

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, @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. 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, @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 Pairings at 8 Chains North Winery

8 Chains North Winery carries chocolates from local chocolatier and restaurant, The Conche, which can be paired with your tasting for only $7 more. Seasonally, they offer special food and wine pairings from bruschetta boards to their popular, annual Girl Scout Cookie and Wine pairing. 

Soothe Your Senses at Purple Wolf Vineyard


Photo Credit: Chad Williams, @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.