There’s no better place to spend Autumn than in New England. The quaint towns, historic homes and winding country roads seem extra charming dressed up with colorful leaves and pumpkins. My favorite place in New England to visit in the fall is the bucolic town of Woodstock in Vermont. While I love visiting Woodstock in fall, it is a beautiful place to visit year round! This Woodstock, Vermont travel guide covers how to plan a great getaway to this charming town, and the information can be applied to all seasons! I’m sharing the best things to do, the not-miss restaurants and my favorite place to stay in Woodstock, Vermont. Here’s your travel guide to Woodstock, Vermont!
About Woodstock
Woodstock, Vermont was settled in 1768. It’s an incredibly charming small town with preserved 19th century Victorian mansions, covered bridges and picturesque maple and cheese farms. It was named “The Prettiest Small Town in America” by the Ladies Home Journal magazine, and it really lives up to that title. Walking around the downtown, you can’t help but feel like you’re in a postcard!
Woodstock is located in the center of Vermont, nestled in the Green Mountains. It’s a beautiful town that’s extremely photogenic. The Ottauquechee River winds its way through and there are plenty of back country roads, old farms and covered bridges to really bring the New England charm. Downtown Woodstock is full of historic homes with white picket fences lining the street; it’s exactly what you think of when you picture “small town America.”
Woodstock is a great place to visit year-round, but it really shines in the fall when residents dress their homes and stores in fall decorations. I love walking around the downtown and admiring the seasonal displays! While Woodstock isn’t large, it’s a destination I visit year after year in October, and it never gets old!
Getting to Woodstock and getting around
Woodstock is a five hour drive from New York City. It’s the perfect weekend escape because it’s close enough to make for an easy drive on a Friday afternoon, but feels worlds away from the hustle and bustle of Manhattan’s streets. If you’re coming from further away you can fly into Boston or Manchester and rent a car to drive to Woodstock. A car is necessary in Vermont as there aren’t many taxi options. The center of town is very walkable, but to visit farms and other picturesque locations you’ll need to drive.
Where to stay in Woodstock
The best hotel in Woodstock is The Woodstock Inn and Resort, which is conveniently located in the center of downtown. The Woodstock Inn is a luxury resort with elegant accommodations, a spa, golf course and four restaurants (one that’s AAA Four-Diamond rated). The resort has a strong history in the Woodstock community. It was established by Laurance and Mary Rockefeller and the original Inn was built in 1892. It’s a beautiful inn with exquisite grounds that are beautifully decorated for each season. I recommend The Woodstock Inn and Resort for its superb customer service, beautiful decor and grounds and laid back atmosphere. You can read my thorough review of The Woodstock Inn and Resort here.
What to do in Woodstock
Walk around the downtown– Exploring the charming downtown area of Woodstock is a must. There are so many cute clothing stores, delicious local food shops and fun gift stores. If you stay at The Woodstock Inn you can walk right to all that downtown has to offer! I especially love the Vermont Flannel Company store and had fun trying on various patterns. Another store I recommend is Farmhouse Pottery, which is just outside of downtown. It’s well worth the short drive. As I mentioned fall is a great time to visit Woodstock due to the autumn decorations. You’ll spot lots of beautifully decorated houses scattered throughout the downtown. My favorite covered bridge, Middle Cover Bridge, is also located right in the center of town.
Photography– Woodstock is a very picturesque town. Any photographer would have a field day, as every time we turned a corner there was another beautiful location. My favorite photo spots in Woodstock are:
Sleepy Hollow Farm- The most famous farm in Woodstock. It’s located on Cloudland Road.
Middle Cover Bridge- Right in the center of downtown. The sun can be harsh here, so keep that in mind.
Downtown Woodstock homes and gardens
Woodstock Inn and Resort grounds
Visit farms– There are a lot of farms surrounding the Woodstock area. Sugarbush Farm is known for its maple syrup and cheese. Sugarbush has a large sampling room to taste the products and learn about the creation process. Billings Farm and Museum is regarded as one of the best outdoor history museums in Vermont. Here you’ll find barns and exhibits to tour including a farm manager’s house from the 1890’s.
Hike– Woodstock is located in the Green Mountains, and there are many great hiking trails. The most popular hike in Woodstock is the Mount Tom Trail. It’s a moderate 4.2 mile heavily trafficked loop trail that features a lake.
Check out a brewery– Vermont is known as a great state for craft beer. Some of the best breweries located near Woodstock are Long Trail, Harpoon and River Roost.
Where to eat and drink in Woodstock
Worthy Kitchen– This is a great spot for lunch or a casual dinner. Worthy Kitchen serves up an inventive menu filled with unique sandwiches, comfort food and an expansive craft beer list. It gets very crowded during weekend afternoons in high season (summer and fall), so keep that in mind.
Abracadabra Coffee– This is a local specialty coffee roaster. It’s located in downtown Woodstock and serves the best coffee in town.
Long Trail Brewery– Perfect for any craft beer aficionado, Long Trail is a great spot for a pint. The brewery offers tours and also has a menu full of standard bar fare.
Dr. Coburn’s Tonic– This bar and restaurant is located in the center of downtown and serves classic pub food and strong drinks. It’s a great spot for happy hours.
Mon Vert Cafe– My favorite place downtown for breakfast or a quick lunch. They also serve speciality and seasonal coffee drinks.
Melaza Bistro– This colorful Caribbean restaurant is one of my favorites in Woodstock! It serves delicious and flavorful Caribbean foods such as arroz con pollo and paella.
Love the pics. My daughter and I went on a 10 day trip to Vermont and New Hampshire. Woodstock was one of our fav places!!!
Great info, thxs. My sister and I went 3 yrs ago in the winter. We thinking of going in the fall this yr.
Can I ask what your travel dates were for Vermont? Currently planning a trip for the last week of October and a bit worried we will miss all the foliage…..
Hi Brittany! You’re right, end of October is a little too late. I try to visit in early October to see the height of the foliage. Vermont will still be beautiful end of October, but a lot of the leaves will likely have fallen.