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Vermont 7 Day Travel Itinerary

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Barn | Back Roads of Vermont | Vermont 7 Day Travel Itinerary | New England
Back Roads of Vermont

Vermont is a New England state known as much for its socially progressive personality as for its forests, dairy farms, and covered bridges. Vermont’s landscape is a mosaic of mountain terrain, colonial-style villages, logging trails, and ski slopes. Our Vermont 7-Day travel itinerary focuses on things to do in Vermont in summer and fall.

Vermont Road Trip | Vermont Itinerary Summer | Vermont Travel Guide
Vermont Road Trip

Vermonters tend to be passionate about all things locally-made and/or raised. This makes for a dynamic shopping and food scene. Vermont has a committed farm-to-table food movement. Whether frequenting a local diner or 5-star restaurant, the cuisine is likely to be locally sourced and fresh.

Village Farm, Brownsville VT | Vermont 7 Day Travel Itinerary | New England
Village Farm, Brownsville VT
Vermont 7 Day Itinerary At A Glance | New England, USA

For more information on New England travel destinations read our articles on:

Rocking Chairs | Woodstock VT | Vermont Travel Itinerary | New England
Rocking Chairs | Woodstock VT


Organic farms and red dairy barns dot Vermont’s rural landscape. Country roads weave through pastures, stands of maple trees, and sugar houses. Our Vermont itinerary – summer focuses on Windsor County in the south-central region of the state. Using the town of Woodstock as a base, our Vermont travel guide takes in 4 covered bridges, 2 mountains, and many charming villages.

Antique Shopping | Things to do in Vermont | New England Travel Destination
Antique Shopping

Vermont is a popular four-season New England travel destination. During the winter, skiers flock to the mountains. The state draws hikers and bikers during the summer. Leaf-peeping is big business in autumn. For many travelers, spring is the least favorite season to visit due to the mud, mosquitoes, and brown landscapes.

Maple Sugar | Vermont Itinerary | Vermont Travel Guide | New England
VT Maple Sugar

Central Vermont has some public transportation. However, like many locations in New England, train and bus options can be sparse. A private vehicle is recommended to best enjoy the area.



Woodstock is known as one of the state’s prettiest towns. Joe and I recommend using a Woodstock, Vermont hotel as your travel base. Woodstock’s walkable downtown is full of unique shops, art galleries, and eateries to enjoy after a day of sightseeing.

Hiking Trail | Vermont Itinerary Summer | New England Travel
Hiking in VT

Woodstock sits at the base of the Green Mountain National Forest. The town is within a half-hour of Interstate’s 89 and 91. It sits on Route 4, the Crossroads of Vermont Byway. Along this stretch of road there are luxury resorts, historic B&Bs, and family-run hotels to choose from at a variety of price points.

Vermont Travel Guide | Farm Stand | Vermont Road Trip
Farm Stand


Day 1: Explore Woodstock Vermont

Woodstock, Vermont is the quintessential New England village. It's a great place to start your Vermont travel itinerary. Begin your day with an ala carte or breakfast buffet at the Woodstock Inn’s Red Rooster Restaurant. It’s a fun and affordable way to spend a bit of time at this iconic and luxurious landmark.

 Woodstock Inn and Resort | Vermont Travel Itinerary | New England Travel Destination
Woodstock Inn and Resort

After breakfast, walk across the town green to Middle Covered Bridge. Then spend the afternoon shopping Woodstock’s downtown. Central and Elm Streets are full of one-of-a-kind businesses like the F. H. Gillingham General Store, Unicorn’s, and Woodstock Hops N Barley.

Woodstock Vermont | Vermont Itinerary | Things to do in Vermont
Woodstock, Vermont

If you are looking for an outdoor activity, rent a pedal or e-bike at Woodstock Wheels. Bikes rent for 2-hour, 4-hour, and all-day increments. Maps and routes are available to help plan a ride.

Have dinner at a restaurant in town. We recommend the Prince and the Pauper Restaurant.

Prince and the Pauper Restaurant | Woodstock Vt | Vermont 7 Day Travel itinerary
Prince and the Pauper Restaurant

Day 2: All Things Quechee

(Antiques Collaborative, Gorge, Village, and Covered Bridge)

It’s a day to explore all things Quechee! Begin at the Antiques Collaborative in the neighboring village of Quechee. At the Collaborative, over 165 dealers on three floors display a wide array of collectibles and antiques.

Quechee Antiques Collaborative | Vermont 7 Day Travel Itinerary | New England Travel Destination
Quechee Antiques Collaborative

A short distance down Route 4, visitors will find the Quechee Gorge State Park. The Vermont attraction is a 165’ ravine that is sometimes called the “Grand Canyon of the East.” Tourists can view Quechee Gorge on a bridge that spans the Ottauquechee River. There is free parking at either end of the bridge. Other area activities include hiking a river trail through the State Park, and Segway Tours.

Quechee Gorge | Vermont Travel Itinerary | Vermont Summer Attractions
Quechee Gorge

Further along Route 4, is another popular Vermont attraction. Quechee Gorge Village is a collection of Vermont-themed stores, restaurants, and attractions. The village has a General Store with a toy museum and expansive antique shop. Onsite there is a winery, brewery, and farm stand.

Quechee Gorge Village | Vermont 7 day Travel Itinerary | New England Travel Destination
Quechee Gorge Village

After stocking up on maple syrup, Cabot cheese, and souvenirs, stop for a bite at the Public House Restaurant. This colorful pub serves up comfy pub foods and regional favorites.

Quechee General Store | Vermont Itinerary Summer | Things To Do in Vermont | New England
Quechee General Store

Wrap up your Vermont road trip in the tiny village of Quechee. Park at the Quechee Covered Bridge Park. Take some time to explore the Quechee Covered Bridge and Mill Falls Waterfall. Then, check out the nearby Simon Pearce Factory Store. After viewing the glassworks showroom, locate the company restaurant that overlooks Quechee Covered Bridge and enjoy a meal.

Simon Pearce and Mill Pond Falls | Quechee Vermont | Vermont 7 Day Travel Itinerary
Simon Pearce and Mill Pond Falls

Day 3: Brownsville & Mount Ascutney

One of the best things to do in Vermont in the summer is hike. Today, the itinerary calls for a scenic 11-mile drive through Winsor County from Woodstock to Brownsville’s Mount Ascutney. Take Route 106 through stunning forests and farm country to the Mount Ascutney State Park.

Fire Tower Mt. Ascutney | Vermont Travel Itineraries | New England
Fire Tower Mt. Ascutney

Drive the 3.7-mile Mount Ascutney Parkway road up the first 2800’ of the mountain. Then, park the car and hike the last mile to the 3144’ summit. Climb the fire tower for spectacular views of the valleys below. Serious hikers can locate a trailhead at the bottom of the mountain, and spend the day hiking.

Hang Glide Platform - Mt. Ascutney | Vermont Itinerary Summer | Vermont Travel Guide
Hang Gliding Platform Mt. Ascutney

Day 4: Windsor & the Windsor Artisans Park

Start the day with a Vermont road trip to the rural town of Windsor. Walk the small downtown and have breakfast at the Windsor Diner.

Next, journey to the Windsor Artisans Park. The collection of Vermont-based companies is a major shopping destination. Stores include Harpoon Brewery where you can watch craft beers being brewed and Simon Pearce Glassworks and Pottery where visitors can observe glass being blown.

Craft Beer | Harpoon Brewery | Windsor Artisans Park | Vermont Things To Do
Harpoon Brewery

Onsite there is also SILO Distillery, Path of Life Sculpture Garden, Great River Outfitters, Blake Hill Preserves, and Artisan Eats. Stroll the park and stock up on gifts for the holidays. Parking is free at the Artisans Park.

Great River Outfitters | Windsor Artisans Park | Vermont 7 Day Itinerary | New England
Great River Outfitters

Day 5: Billings Farm Museum & Mansion Tour

Today, experience a bit of Woodstock’s beautiful outdoors. The first stop on the itinerary is Billings Farm Museum. The well-respected living outdoor museum teaches about 19th century and modern-day farm life in Vermont.

Indoor museum exhibits are displayed in a three-story barn complex. Outdoors, visitors can tour expansive gardens, pastures, and working dairy barns.

Exhibit | Billings Farm Museum | Vermont Travel Guide | Things to do in Vermont
Exhibit | Billings Farm Museum

Across the street from Billings Farm, walk to the Marsh-Billings-Rockefeller National Historic Site. The site features an 18th century estate that can be toured including a mansion, greenhouse, and gardens. The acreage behind the mansion includes 20-miles of hiking and ski trails. Stretch your legs with a trek through the beautiful Vermont woods.

For spectacular views, experienced hikers will enjoy a hike up the 1359’ Mount Tom which is located inside of the park.

Mansion | Marsh Billings Rockefeller National Historic Site | Vermont Attractions Summer
Marsh Billings Rockefeller National Historic Site

Day 6: Scenic Drive to Killington Ski Resort

Our Vermont itinerary for today involves another road trip. Follow scenic Route 4 about 30-minutes west of Woodstock until reaching the Killington Ski Resort. Look for signs to the K-1 base lodge and Killington Gondola. The aerial gondola lift is a popular Vermont summer attraction. It takes visitors up the mountain to about 4,140 feet. From there, a short 10-minute hike will take you to the 4,241’ summit of Mount Killington. On a clear day the views feel infinite.

Day 7: Scenic Drive of Central Vermont’s Covered Bridges

Spend your last day in Vermont admiring its iconic covered bridges. Our road trip today will take you to two more covered bridges: Taftsville and Cornish-Windsor.

Taftsville Covered Bridge, Windsor County | Vermont Travel Itinerary | New England, USA
Taftsville Covered Bridge

The first stop will be at the Taftsville Bridge in Hartford. From here, take backroads to the Cornish-Windsor Covered Bridge on the Vermont-New Hampshire Border. Spend the remainder of your last day stopping at any farm stands, sugar houses, or gift shops that tickle your fancy.

Cornish-Windsor Covered Bridge "Walk Your Horses or Pay Two Dollars Fine" | Vermont Attraction
Cornish-Windsor Covered Bridge

Hope you enjoy all the great food and vegetarian options, Laura and Randy

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