Things to Do in Woodstock, Vermont

Oh, how I love Vermont! It makes me happy just thinking about it. It has gorgeous forests, charming towns, and inspiring artisan culture. Located in southern Vermont, the area around Woodstock is very convenient to the rest of New England, and this area embodies all that I love about Vermont.

If you are searching for romantic getaways in Vermont, this area is the place to visit– historical, artistic, and quaint.

I visited the area around Woodstock for a perfect fall weekend girls’ getaway. We stayed in South Woodstock, a village of Woodstock, in a friend’s home in a restored mill. We came at peak foliage season, which is the ideal time to visit the area, although there is great skiing for a winter visit as well.

Girls weekend in Vermont.
Me and the girls during our fall weekend in Vermont.

My family also drove through this area on our road trip from Boston to Montreal and Quebec City.

Read on to plan your perfect Vermont getaway.

Things to do in Woodstock, Vt

Day One of our Weekend around Woodstock, Vermont

Explore the Village of South Woodstock

South Woodstock is a small village that is part of Woodstock. The village is tiny but also feels like an escape from reality. We started our day with a refreshing walk past the old houses to breakfast at the South Woodstock Country Store.

South Woodstock Country Store
things to do in southern Vermont
South Woodstock Country Store

Not only can you find unique goods and foods in this authentic country store, they serve inexpensive but scrumptious food at their take-out counter. They have tables to eat at where you can enjoy locals chatting. We enjoyed our egg sandwiches and the atmosphere so much that we came here both days for breakfast.

Exploring Downtown Woodstock, Vermont

Vermont getaway
Downtown Woodstock, Vermont

We spent the first day of our weekend in Woodstock. This town has often been called “the prettiest small town in America” and the quintessential New England town– and for a good reason. Walk along the main street, Central Avenue (Route 4), taking any deviations that excite you. The word meandering is made for this town, so that is what we did.

Shopping in Woodstock, Vermont

Around the town green in Woodstock, you will find many stores offering all your heart desires, from food and clothing to flowers and art.

FH Gillingham & Sons Vermont Country Store
What to do in Vermont
Some of the treats at FH Gillingham & Sons, Woodstock, Vermont

You will find unique foods, clothing, games, and pet supplies in this country store. It is the perfect spot to pick up a souvenir.

Norman William’s Public Library

Vermont weekend getaway

This public library is on the town green, with placards about the town’s history that are worth checking out. There is a used book sale in the alcove in front of the library, and I picked up one of my recent favorites, The Russian Concubine. Read about more of my favorite books.

Middle Bridge

You can’t come to Vermont without seeing at least one of the bridges it is so famous for– a covered bridge. There is one in town over the Ottaquechee River, Middle Bridge.

Dinner Around Woodstock, Vermont

Now that we had spent the day in town, we wanted to get away from civilization and see some spectacular views. We enjoyed the four-mile drive up the mountain to enjoy a farm-to-table gourmet meal at Cloudland Farm in North Pomfret. The farm has miles of Appalachian Trails, which are open to the public, so if you have time, you can earn your dessert calories with a pre-dinner hike. Reservations are required for dining.

One Day in Quechee, Vermont: Hiking and Art

For our second day in Vermont, we decided to explore the area around Quechee, specifically the artisans and the gorge. Our day started with egg sandwiches at South Woodstock Country Store before heading towards the Quechee Gorge for a short hike.

Vermont Antique Mall

We first stopped at the Vermont Antique Mall with a Cabot Cheese Shop. You can also try locally-produced wines and fudge. Be sure to pet the alpacas behind the store.

Quechee River Gorge

Things to do in Quechee, Vermont
Quechee River Gorge in autumn

Quechee Gorge is the deepest gorge in Vermont at 165 feet deep. There are fantastic views of the gorge from the bridge on Route 4 that crosses it. We took the pretty easy half-mile hike along the Quechee Gorge to reach the bottom. You can also camp here.

Woodstock Farmer’s Market

We stopped and grabbed lunch at the Woodstock Farmer’s Market. Although it is called a farmer’s market, it is more of a locally-sourced market with a deli counter. It won’t be a problem finding something yummy to eat here. The hard part is picking between all the great choices. We grabbed salads, sandwiches, and soups.

After lunch, we stopped by the see the Vermont artists at work.

Farmhouse Pottery

We stopped and watched the potters turn lumps of clay into beautiful cups and vases. You can buy the products in the store.

Andrew Pearce Bowls

Then we moved on to watching wooden bowls being made from local trees.

Sugarbush Farm

Another spot to try local foods- farm-made waxed cheeses and maple syrups!

The Mill at Simon Pearce

Where to eat in Woodstock, Vermont
I am still Jonesing for this perfect bowl from Simon Pearce.

Everything about this mill set on the Ottauquechee River is magical. We started downstairs, where glassblowers are working hard to create some of the prettiest glass creations I have ever seen. Be sure to step out on the patio to see the Ottauquechee River waterfall, which provides power for the mill and flows right under a covered bridge.

The food in the dining room is American at its best, and the views are incredible. After dinner, we did some lustful shopping throughout the showroom.

Day Breaks Glass Studio

Try your hand at making stained glass with a class at this studio in Lebanon, Vermont.

places to visit in Vermont
Our dinner view from the dining room at Simon Pearce

Where to Stay in Woodstock, Vermont/ Woodstock, Vt Hotels

Woodstock Inn & Resort, Woodstock, Vermont

Woodstock Vermont hotels
Woodstock Inn, Woodstock, Vermont

Stay in the Woodstock Inn if you are looking for luxury right in downtown Woodstock. Even if you don’t have the money to stay, you should take the time to walk through the adorable inn. It is definitely one of my bucket list hotels.

Book your room at The Woodstock Inn now.

Quechee Inn at Marshland

If you are looking for more moderately priced accommodations, this colonial farm with many activities is a great option.

Book a room at the Quechee Inn now.

Kendron Valley Inn

This charming small hotel is right in South Woodstock. It has a fantastic upscale pizza restaurant. Pets are allowed in cabins behind the main hotel.

Book a room at the Kendron Valley Inn now.

Here is a map to understand where the things we did are in relation to each other:

As you can see, there are so many unique, charming, tasty outdoor things to do in southern Vermont–even if it is not winter with its nearby skiing!

Have you been to this area of Vermont? Please let me know about it in the comments if you have anything to add.

If you are visiting Vermont as part of a trip to New England, be sure to check out my Local’s Guide.

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6 thoughts on “Things to Do in Woodstock, Vermont”

  1. We have been planning to visit Vermont for some time. I can see we need to add Woodstock to the plan when we finally do visit. Definitely fall would be a perfect time to visit. We love those old town main streets for unique finds.

  2. Woodstock looks delightful. I haven’t been to Woodstock specifically, though we did have a leaf-peeping trip to Vermont a few years ago and absolutely loved it. I can see Woodstock would definitely be worth visiting with so many delicious local foods to sample and the wonderful artisan products to browse. That bowl is beautiful!

  3. Don’t forget to check out other stores in Woodstock like primrose, the unicorn and the VT flannel Co. Visit the reading greenhouse farm market in reading, VT, Great food at Chef Brad’s “crazy side” in Quechee. And check out OQ Farm in Woodstock for a possible family reunion place to stay. Other great eats… Claude’s, Casey’s caboose, in Killington (Claude’s is the BEST). And in Rutland don’t forget the Palms.


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