14 days in Vermont & Connecticut Itinerary

14 days in Vermont & Connecticut Itinerary

Created using Inspirock United States tour planner
Make it your trip
— 2 nights
Saint Johnsbury
— 2 nights
— 2 nights
— 2 nights
— 5 nights


Burlington — 2 nights

Burlington is the most populous city in the U.S. state of Vermont and the seat of Chittenden County. Kick off your visit on the 19th (Mon): stroll around Waterfront Park, then steep yourself in history at Shelburne Farms, and then experience rural life at Country Dreams Farm. Get ready for a full day of sightseeing on the 20th (Tue): hike along Burlington Bike Path and then browse the eclectic array of goods at Church Street Marketplace.

To see traveler tips, maps, more things to do, and other tourist information, go to the Burlington visit planning app.

Anchorage to Burlington is an approximately 13-hour flight. You can also drive. You'll lose 4 hours traveling from Anchorage to Burlington due to the time zone difference. Plan for a bit warmer temperatures traveling from Anchorage in September, with highs in Burlington at 75°F and lows at 53°F. Finish your sightseeing early on the 20th (Tue) so you can drive to Saint Johnsbury.
Parks · Historic Sites · Outdoors · Shopping
Side Trips

Saint Johnsbury — 2 nights

St. Kick off your visit on the 21st (Wed): explore the world behind art at St. Johnsbury Athenaeum and then admire the striking features of The Dog Chapel. Get ready for a full day of sightseeing on the next day: look for gifts at Chutters and then explore the activities along Lake Willoughby.

To see maps, more things to do, reviews, and more tourist information, use the Saint Johnsbury route planning website.

Traveling by car from Burlington to Saint Johnsbury takes 2 hours. September in Saint Johnsbury sees daily highs of 72°F and lows of 49°F at night. Finish your sightseeing early on the 22nd (Thu) so you can drive to Woodstock.
Museums · Shopping · Nature · Parks
Side Trips

Woodstock — 2 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Kick off your visit on the 23rd (Fri): pause for some photo ops at Saint-Gaudens National Historic Site, take in the dramatic natural features at Quechee Gorge, and then admire the majestic nature at Quechee State Park. Keep things going the next day: get engrossed in the history at Billings Farm & Museum and then relax in the rural setting at Sugarbush Farm.

To find reviews, more things to do, ratings, and more tourist information, go to the Woodstock trip planner.

Traveling by car from Saint Johnsbury to Woodstock takes 1.5 hours. In September, plan for daily highs up to 75°F, and evening lows to 50°F. Cap off your sightseeing on the 24th (Sat) early enough to go by car to Manchester.
Historic Sites · Nature · Parks · Museums
Side Trips

Manchester — 2 nights

Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. On the 25th (Sun), get engrossed in the history at Hildene, The Lincoln Family Home and then take in the dramatic scenery at Lye Brook Falls. Keep things going the next day: take some stellar pictures from Bennington Battle Monument and then admire the masterpieces at The Clark Art Institute.

To find ratings, reviews, photos, and tourist information, use the Manchester online driving holiday planner.

You can drive from Woodstock to Manchester in 1.5 hours. Another option is to take a bus. In September, daily temperatures in Manchester can reach 74°F, while at night they dip to 48°F. Wrap up your sightseeing on the 26th (Mon) early enough to drive to Mystic.
Museums · Historic Sites · Nature · Parks
Side Trips

Mystic — 5 nights

A historical leading seaport, Mystic has maintained a strong respect for the past.
Explore the numerous day-trip ideas around Mystic: ShelaLara Winery Tour & Tasting (in Coventry), The Mark Twain House & Museum (in Hartford) and Taylor Brooke Winery (in Woodstock). There's lots more to do: look and learn at Mystic Seaport Museum, contemplate the long history of Olde Mistick Village, try to win big at Foxwoods Resort Casino, and look for gifts at The Spice & Tea Exchange.

To see traveler tips, other places to visit, and more tourist information, you can read our Mystic planning site.

You can drive from Manchester to Mystic in 4 hours. Other options are to drive; or do a combination of flight and train; or do a combination of bus and train. Traveling from Manchester in September, you can expect nighttime temperatures to be somewhat warmer in Mystic, with lows of 58°F. Finish your sightseeing early on the 1st (Sat) so you can fly back home.
Museums · Tours · Historic Sites · Shopping
Side Trips

Vermont travel guide

Gift & Specialty Shops · Ski Areas · Hiking Trails
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.

Connecticut travel guide

Aquariums · Theaters · Observatories
The Constitution State
Perhaps best known for its renowned private and public universities, Connecticut was once home to the country's first law school and still boasts one of the oldest secondary schools in America. More than just a small state packed with students, Connecticut offers visitors a chance to explore some of New England's finest tourist attractions while on vacation, including lighthouses, beaches, theaters, museums, galleries, and restaurants. Despite its small size, the state also boasts two large casino complexes, both located on Native American reservations. Rich in history and natural beauty, Connecticut draws newcomers from around the world, with large Polish, Chinese, and Hispanic communities.