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Nestled about halfway in the Shenandoah Valley, lies the charming town of Woodstock, VA, in Shenandoah County. The friendly small town is perfectly situated to enjoy both nature and town life. Located just an hour and a half west of Washington, DC, Woodstock makes for a quick getaway from the big city. Whether you’re coming from Virginia, North Carolina, Maryland, or West Virginia, you’re never too far away from a fun weekend in Woodstock, VA.
Whether you’re a lover of the outdoors or like discovering charming small towns, you’ll find something to do in this town. Check out all the fabulous things you can do in Woodstock, VA.
Best Things to Do in Woodstock, Virginia
1. Admire the scenery from the Woodstock Tower
Nature lovers will delight in observing the breathtaking view from the Woodstock Tower. A short drive and a few minutes hike are all that separate you from one of the best spots in the entire Shenandoah Valley – the Woodstock Tower.
Don’t forget your camera as you enjoy views of the Seven Bends of the Shenandoah River from the Woodstock Tower and viewing platforms.
PRO TIP: Visit during the fall to obtain gorgeous foliage views like the ones in my photo!
2. Enjoy a glass of wine at Muse Vineyards
Due to its location in the Shenandoah Valley, Woodstock and neighboring areas enjoy a perfect situation for growing grapes. You’ll find a variety of wines, from whites to reds, and a few sparkling wines included.
Owned by a husband and wife who bought an overgrown vineyard in 2003, Muse Vineyards creates award-winning wines. Muse offers a few types of pre-selected flights for those who want to sample, as well as light nibbles. During the weekend, a food truck may offer heartier offerings. Grab your glass and sit on the upstairs deck, where you’ll enjoy a view of the fabulous vineyards.
PRO TIP: Visit on Thursday and Friday evenings when Muse offers a sunset dinner.
3. Take a selfie with a LOVE sign
Virginia is for Lovers, and like other Virginia destinations, Woodstock participates in the program with not one but TWO beautiful LOVEwork signs. The newest LOVE sign is found at the Seven Bends State Park. The rustic nature of the sign highlights everything great about this park.
The original LOVEwork sign is found at 614 N. Main Street, on the campus of the Massanutten Military Academy. The sign reflects the town’s identity. The L is a Swiss guard who has been the town’s symbol for years. The O is a hot air balloon because, on clear days, you’ll see them dotting the sky as they float over the Shenandoah Valley. The green V represents the town’s commitment to keeping it green – from beautiful parks to preserving its Tree City USA status. The E is the fabulous Woodstock Tower – which needs to be a stopping point for every visitor in town.
4. Take a leisurely (or not so leisurely) stroll through Seven Bends State Park
The Seven Bends State Park is open daily from 6 am until dusk. Two entrance points are clearly marked as you drive on Main Street – Lupton Access and Hollingsworth Access. The park has 8 miles of walking trails that are clearly labeled, easy to follow, and have various difficulty levels. The park’s ease of access and beauty make this visit one of the best things to do in Woodstock, Virginia.
The LOVE sign pictured above is found near the Lupton Access parking lot. I recommend picking up a tasty breakfast treat and coffee from Flour & Water to enjoy while you wander the trails.
PRO TIP: You’ll need a state park pass to enjoy the facilities. You’ll use self-pay with cash or with a QR code at the park.
5. Grab breakfast at Flour and Water
Also located downtown Woodstock on Main Street is Flour and Water, a local bakery and coffee shop. Showcasing European-style baked goods, make sure you pack your stretchy pants before visiting! But pastries aren’t the only thing baking here – Flour and Water offers breakfast, lunch, and even a Wednesday night pizza menu! Take some cookies or a fresh loaf of bread home for a snack later.
6. Stroll along Main Street for some shopping
I love an easily walkable Main Street dotted with boutiques and shops – and Woodstock delivered! One of my favorites was Travelers Treasures with its unique Woodstock souvenirs. Whether you’re looking for a new outfit for your evening out, something to wear for hiking, a local trinket or two, Woodstock’s Main Street will delight your shopping tastes.
7. Enjoy a local meal at Woodstock Cafe
Located on Main Street, Woodstock Cafe is perfectly situated in the middle of downtown as a place to grab breakfast/brunch or lunch. Woodstock Cafe serves a variety of foods from sandwiches to salads to breakfast standards. If you can, visit them Thursday through Sunday when they offer delicious homemade pasta dishes (make a reservation!).
8. Enjoy a tall cool beer at Woodstock Brewhouse
After you’ve explored a bit, enjoy dinner and a cold brew at Woodstock Brewhouse. As a craft beer lover, I enjoyed a flight of their beers. Offering nine flagship beers of varying styles, along with almost as many seasonals and rotating beers, the beer lover in your group is sure to find a new favorite.
9. Admire art at 7 East Gallery
Located at the Valley Education Center for the Creative Arts (VECCA) on Main Street downtown, art lovers will find all kinds of artisan offerings from local artists. You can check out their calendar in advance and add an evening class to your Woodstock visit.
10. Enjoy dinner at Spring House Tavern
If you’re looking for another place for dinner, consider Spring House Tavern, an 18th-century inn located on Main Street. The Tavern has received accolades as having the best restaurant, bartender, steak, and burger in town! But probably the most popular item on the menu are the crab cake bites. Guests also rave about the brunch offerings on Sunday – praising the cinnamon rolls.
11. Check out harness races at Shenandoah Downs
What are harness races? These horse races feature a rider in a buggy (called a sulky) behind the horse instead of on the horse. Shenandoah Downs takes you back to a simpler time as you watch (and bet if you choose) a more traditional horse race. And attending a harness race at Shenandoah Downs is one of the most unique things to do in Woodstock, Virginia.
Grab a hot dog, and a soda, and cheer on your favorite jockey and horse, as this is a family-friendly event.
The season lasts from mid-September to the end of October, perfect timing for those exploring Woodstock in the fall. But check the schedule since Shenandoah Downs also offered a spring season in 2023 and there are special events also during fair week.
12. Learn about bourbon at Filibuster Distillery
Those exploring Shenandoah Valley through its craft beverage trail will undoubtedly want to stop Filibuster Distillery. Located just outside Woodstock in Maurertown, this unassuming distillery will surprise visitors with its offerings and interior. Guests can sample a variety of liquors made right on-site – including a variety of award-winning bourbons. The best part is the knowledgeable employees who will gladly explain the different offerings and how they’re made.
13. Explore trails at the George Washington National Forest
Nature lovers will find plenty to delight them in Woodstock the George Washington National Forest. The Forest offers trails open to horse riders, bicycle riders, and hikers. You’ll find a variety of trails with various difficulties leading you to discover amazing panoramas, connecting to the Appalachian Trail, and even discovering some waterfalls.
14. Hike Big Schloss
Located in the George Washington National Forest is a popular outcropping of rocks named Big Schloss. Hikers undertake a relatively easy 4.4 mile that rises 1000 feet. Plan on the hike taking approximately 4 hours. Pack a lunch or a snack and plan on sitting around for a bit while enjoying the gorgeous views of the valley below.
PRO TIP: Big Schloss is a popular destination and can get crowded during the summer and weekends. Consider hiking Tibbet Knob if you want less crowds, as it offers the same gorgeous views and starts from the same parking lot.
15. Be transported to Europe at North Mountain Vineyards and Winery
North Mountain Vineyards and Winery, located just outside town in Maurertown, focuses on German-style wines. Located inside a former home, North Mountain is an intimate setting where you can even order a special picnic. Not sure which wine you like? Purchase a flight or ask for a tasting. The Spiced Holiday Wine will transport you to an idyllic European Christmas Market.
16. Shop fresh at Mowery Orchard
Located on Route 42 in Woodstock, Mowery Orchard offers a variety of locally grown products year-round. This family-owned market also sells flowering and garden plants. Check out the metalwork and wood carvings produced by Tom, the orchard manager. Don’t you love a local market?
17. Check out a local festival
Check Woodstock’s events calendar for fun activities. Bring your dog to Woofstock. Or bring a chair to enjoy the summer monthly concert series. I visited during Halloween on Court Square, where it seemed the entire town came out in their costumes to go trick-or-treating! With so many fun options, attending a local festival is one of the fun things to do in Woodstock, Virginia.
Visiting during October also allowed me to check out the pumpkin head people. That’s right, every October the entire town gets to create a public art display using a pumpkin for the character’s head. People were really creative, as you can see from the photo!
18. Ride a Hot Air Balloon
One of the best ways to enjoy the scenic Shenandoah Valley is to see it from above – from a hot air balloon! Located just down the road in Edinburg, Valley Ballooning takes visitors up in the air to view the entire Valley. You’ll get to take awesome photos of the Seven Bends River, the Appalachian Mountains, and of course, all the vineyards! This is a unique way to explore the area surrounding Woodstock.
19. Shenandoah County Historic Courthouse
Did you know that the oldest courthouse west of the Blue Ridge mountains is found in Woodstock VA? As an admirer of courthouses, I was delighted to learn that the Shenandoah County Historic Courthouse served as a courthouse from 1795 until the early 1900’s. The building has since been transformed into a visitor’s information center. The building is open to the public March through December, Thursday through Saturday, from 11 am to 4 pm.
20. Drive on historic Route 11
Who needs Route 66 when the Shenandoah Valley has Route 11? While US Route 11 connects a US-Canadian border point in New York to New Orleans, Louisiana. But the bit that passes through Virginia is beautiful and full of history. In Virginia, Route 11 connects Bristol, along the Tennessee-Virginia border, with Winchester near the West Virginia Border.
Route 11 follows a colonial route that became important during the Civil War, connecting north and south. The strategic importance of the road is seen through the eventual parallel I-81 creation. Today, Route 11 connects the towns that dot the Shenandoah Valley, connecting them to bigger destinations too, making driving this road one of the best things to do in Woodstock, Virginia.
PRO TIP: If you’re traveling on I-81 and want to see gorgeous small towns and scenic detours, take Route 11 instead!
Final Thoughts on Best Things to Do in Woodstock Virginia
Woodstock VA exceeded my expectations. The town oozes charm and offers so much to see and do if you’re looking for a great destination in the Shenandoah Valley. It’s a quick hop off I-81 for people driving north-south and the perfect getaway for those in the mid-Atlantic region.
Don’t miss the chance to wander the cozy streets and explore the beauty of Woodstock VA!
Check out these related posts:
- Woodstock Tower – A Can’t Miss Spot!
- 11 Best Woodstock Souvenirs
- A Foodie Destination – Harrisonburg, VA
I want to thank Shenandoah County VA for hosting my visit. As always, my posts accurately reflect my experiences and opinions.
Happy travels,
Annick, The Common Traveler
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Raised as a third culture kid living in South America and Europe, Annick caught the travel bug early. As an empty-nester, Annick enjoys sharing her tips for traveling for those with champagne taste and beer budgets.