5 days in Boston, Maine & Vermont Itinerary

5 days in Boston, Maine & Vermont Itinerary

Created using Inspirock United States trip planner

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Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Start off your visit on the 14th (Thu): stroll around Boston Common, then take in nature's colorful creations at Boston Public Garden, and then take an in-depth tour of Salem Witch Museum.

To find photos, ratings, traveler tips, and other tourist information, read Boston online trip maker.

Miami to Boston is an approximately 5-hour flight. You can also drive; or take a bus. Prepare for much colder weather when traveling from Miami in October: high temperatures in Boston hover around 64°F and lows are around 50°F. Wrap up your sightseeing on the 14th (Thu) early enough to drive to Portland.

Things to do in Boston

Parks · Museums

Side Trip

Find places to stay Oct 13 — 14:


— 1 night

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
To find other places to visit, where to stay, more things to do, and other tourist information, you can read our Portland trip itinerary site.

You can drive from Boston to Portland in 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Boston in October, expect little chillier with lows of 43°F in Portland. You will leave for Stowe on the 15th (Fri).

Things to do in Portland

Outdoors · Parks · Tours · Shopping
Find places to stay Oct 14 — 15:


— 2 nights

The Ski Capital of the East

Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Venture out of the city with trips to Burlington (Burlington Bike Path & Church Street Marketplace). There's much more to do: trek along Stowe Recreation Path, glide through natural beauty at Trapp Family Lodge Outdoor Center, cruise along Smugglers Notch State Park, and take in the dramatic scenery at Moss Glen Falls.

To find other places to visit, where to stay, maps, and other tourist information, read our Stowe trip planning tool.

Traveling by car from Portland to Stowe takes 4.5 hours. Alternatively, you can take a bus; or take a bus. In October in Stowe, expect temperatures between 60°F during the day and 39°F at night. Finish up your sightseeing early on the 17th (Sun) so you can catch the flight back home.

Things to do in Stowe

Parks · Outdoors · Nature · Winter Sports

Side Trips

Find places to stay Oct 15 — 17:

Maine travel guide

The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.

Vermont travel guide

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.