2 Days in Vermont & Where To Stay

woodstock inn resort — Woodstock Inn & Resort in Vermont

2 Days in Woodstock, Vermont

We just returned from spending a weekend in Woodstock, and I am excited to share all about it! Are you considering a trip to Vermont? I love exploring the charming towns and cities of New England, and driving through the state of Vermont during autumn seemed like the loveliest idea, so Woodstock was an easy choice for us!

Crossing covered bridges, tasting Vermont’s famous maple syrup, and seeing the magical colors of fall – that’s what Autumn in Vermont is all about! We came back from Vermont in love, so here is what we did, where we stayed, and what you can expect to see if you go!

In my United States Guides, you will find more ideas for beautiful road trips.

Woodstock – The perfect New England weekend getaway destination.

Where is Woodstock, VT?

Woodstock is located in Vermont, in the New England area of the country.

How far is Woodstock from New York City?

The trip from New York City to the town of Woodstock is around 250 miles (402 km) via I-95 and I-91. The drive took us a little over 4 hours, with normal driving conditions and very little traffic on a Friday morning. If you are visiting Woodstock from Boston, the trip is 140 miles (225 km). Woodstock’s location makes it a perfect weekend destination.

Which airport is best for Woodstock?

Lebanon Municipal Airport (LEB) is 16 miles from Woodstock, a 25 minute drive.

Burlington International Airport (BTV) is 87 miles from Woodstock, a 1+ hour drive.

Another option is to fly into Albany International Airport (ALB) and drive a little over 100 miles to Woodstock.

If you enjoy exploring by car, I suggest flying into Boston Logan Airport (BOS) or any of New York City’s airports and driving up to Vermont.

What is Vermont famous for?

Vermont is well known for its maple syrup, beautiful autumn foliage, mountains, ski resorts, Ben & Jerry’s ice cream, maple creemees, and cheddar cheese.

Why visit Woodstock, Vermont?

Woodstock is incredibly precious all year round! Vermont is also a destination for skiing and snowboarding enthusiasts, so if you find yourself in Killington Ski Resort, the biggest ski resort in Vermont, I recommend adding a stop to Woodstock to your trip (a 30 minute drive).

Where to stay in Woodstock VT?

Woodstock VT Hotels — Woodstock Inn & Resort is one of the best hotels in Woodstock, Vermont.

We stayed at the historic Woodstock Inn & Resort, located just steps from the village of Woodstock. Staying at this resort had been on my bucket list for years, and although snow is typically expected during the month of November, we enjoyed temperatures in the high 60s all weekend long!

The Woodstock Inn is a New England gem that has been cherished for decades. The original property, Richardson’s Tavern, was built in 1793 and renamed The Eagle Hotel in 1830.

Years later, during the tourism boom of the mid-19th century, the new Woodstock Inn was built on the tavern’s original site, quickly becoming Vermont’s first winter sports center for tourists.

Book: Rooms at Woodstock Inn & Resort.

Restaurants-Woodstock-Inn-Resort-Vermont

The Red Rooster – Woodstock Inn’s Restaurant

After an afternoon exploring the Woodstock village, we returned to the hotel for dinner at the Red Rooster, one of the restaurants inside the resort.

The drinks we ordered were excellent, Bees Knees and the seasonal Woodstock Warmer.

I recommend starting with their beet & apple salad (with mint and yogurt dressing!) or the autumn squash soup and having the prime ribeye as the main course. Don’t forget to order dessert, the pumpkin crémeux, and the Maplewood orchard were delicious.

Woockstock Inn — Beautiful details at the Woodstock Inn & Resort.

The Woodstock Inn has been beautifully preserved thanks to the Rockefeller’s generosity and a major renovation in 1967 to modernize the property.

Laurance Rockefeller was a conservationist interested in creating eco-friendly resorts, including the Woodstock Inn in Vermont, and properties in Hawaii, and Wyoming.

How many rooms does the Woodstock Inn have?

The Woodstock Inn has 142 elegant rooms and suites that embrace Vermont’s style.

The resort warmly welcomes dogs and has pet-friendly rooms, so our two pups got to join us on this vacation. 🙂

See the rooms at Woodstock Inn & Resort here.

Shop: Delsey Luggage

Shop: Strathberry Handbag

What to do in Woodstock?

Woodstock is one of the most beautiful towns in New England.

Visit Middle Covered Bridge

Vermont is home to more than 100 covered bridges, more than any other U.S. state! The majority of these bridges were constructed during the mid and late 19th Century.

While visiting Woodstock you can explore Middle Covered Bridge, one of the most picturesque covered bridges in Vermont!

This 139-foot-long bridge is the first public covered bridge built by the State of Vermont since 1889, and breathtaking no matter the season.

You will find this bridge directly across from the Woodstock Inn & Resort, by the Ottauquechee River. After photographing the bridge, be sure to walk over to the Village of Woodstock, where you will find over a dozen of the cutest shops around!

Other covered bridges near Woodstock include Taftsville Covered Bridge, Lincoln Covered Bridge, and Quechee Covered Bridge.

Shop at Local Stores

During our walk around the village of Woodstock, we stopped at as many local shops as we could! I love buying unique gifts to bring back home, and I bought a cheese board, the cutest red jar for serving maple syrup, Christmas decorations made by local artisans, holiday cards, and magnets!

Be sure to stop by F.H. Gillingham & Sons, a New England general store that has been in business for over 130 years, selling everything from jams and maple syrup to clothing and toys. Visiting their store was like stepping back in time!