With a population of just over 5,000, Woodstock is one of the best small towns in Virginia and it has plenty of charm. Woodstock is located in northern Virginia, in the heart of the breathtaking Shenandoah Valley. Established in the 1700s, it’s a town with plenty of history, much of which has been preserved in the historic district. Visitors today will find plenty of things to experience, whether they be outdoor activities, restaurants to try, or shops to visit. Let’s take a look at some of the wonderful things to do in Woodstock, Virginia.

Jimmy Emerson, DVM/flickr
The town of Woodstock was originally part of a land grant from Lord Fairfax and its charter was sponsored by George Washington himself. Needless to say, this place has acquired quite a bit of historical significance in its time.
Doug Kerr/flickr
One of the most prominent features of Woodstock is its architecture. The distinguished buildings offer character and meaning to the downtown area, making for a beautiful walk through town. Photographed above is the historic courthouse, which is the oldest of its kind west of the Blue Ridge Mountains. The original limestone dates back to 1790, and the building itself was designed by Thomas Jefferson.
Rudi Riet/flickr
If you're curious to see the city from a different perspective, you can opt for a hot air balloon ride. Valley Ballooning offers memorable rides that are both exhilarating and informative.
T7622XSkatheyw/TripAdvisor
One of the most popular attractions in town is the Woodstock Tower Observation Site. You'd be hard pressed to find a better view of the Shenandoah Valley in the entire state. Be warned, however, that the drive up is incredibly windy. Just be sure to take your time and admire the views once you're at the top.
Wes M./TripAdvisor

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Wes M./TripAdvisor
Big Schloss is another local favorite, especially among outdoor enthusiasts. The hike is 4 miles total and is rated moderately difficult, although the views will be worth your effort. The hardest part of the hike is the very beginning, but once you've made that elevation gain you can start to enjoy the beautiful surrounding scenery.
Rich C./TripAdvisor
In the mood for browsing some of the town's finest crafts and homemade goods? Be sure to stop by The Market. It sells a little bit of everything, specializing in kitchen wares, coffees, wines, and other specialty goods.
daisyferret1/TripAdvisor
And if you're looking for the perfect spot to enjoy those local goods from The Market, you'll want to take a pit stop at W.O. Riley Park. This family-friendly spot has beautiful grounds for taking a stroll, playing a quick game of tennis, or simply enjoying the day.
Woodstock Brew House/Yelp
Woodstock Brewhouse/Facebook
As the evening approaches, check out Woodstock Brewhouse for some tasty craft beer and live music. Located in the renovated Casey Jones work clothes factory on Main Street, it's a spot loaded with local history.

Whether you’re stopping by for a quick hello or happen to have a whole day to spend in Woodstock, you’ll enjoy choosing among plenty of activities. Here is even more information about what to do in Woodstock, Virginia.

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Things To Do In Virginia

William Suphan | March 22, 2023

What are some lesser-known attractions in Virginia?

Lesser-known attractions in Virginia include:

  • Mount Rogers Recreation Area. This is the highest peak in the state and there are wild highland horses that roam the area.
  • The Old Cape Henry Lighthouse. This was the first lighthouse that the U.S. built in 1792 and it has been rebuilt but still uses the original light.
  • Wilderness Road State Park in Ewing. This is an interactive living history site that shows what life was like for pioneers in the 1700s.
  • James Madison’s Home in Montpelier. This old house was restored in 2008 and the surrounding forest has remained intact since the 1700s.

Learn more about these and other lesser-known attractions in Virginia. 

What are the best free things to do in Virginia?

The best free things to do in Virginia include:

  • Colonial Williamsburg. Come see one of the best living history museums in the country to see colonial Virginia come to life.
  • Bluebird Gap Farm in Hampton. Come here to see and pet many species of animals and see farm antiques that are centuries old.
  • Virginia Beachfront and Boardwalk. Besides the beach itself, there is always some kind of entertainment here, including street performers, live music, and more.
  • Maymont in Richmond. There is a manicured garden, petting zoo, historic mansion, nature center, and much more here.

Discover more about the best free things to do in Virginia.  

What are some bucket list attractions in Virginia?

Bucket list attractions in Virginia include:

  • Appomattox Courthouse. This is the place where General Lee surrendered and it marked the end of the Civil War.
  • Jamestown. This was the first British settlement and there is a ton of history here from the perspectives of the settlers and the Native Americans of the time.
  • Yorktown Battlefield. This was the site of the last battle of the Revolutionary War in 1781 and there are many relics to see.
  • Mount Vernon. This was the home of George Washington where he lived until 1799 and it is now a living history museum.

Find out more about these and other bucket-list attractions in Virginia. 

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Woodstock, VA 22664, USA