57 days in New England Itinerary

57 days in New England Itinerary

Created using Inspirock New England attractions planner

Make it your trip
Fly
1
Bar Harbor, Mount Desert Island
— 5 nights
Drive
2
Rockland
— 3 nights
Drive
3
Portland
— 6 nights
Drive
4
North Conway
— 5 nights
Drive
5
Bennington
— 3 nights
Drive
6
Groton
— 5 nights
Drive
7
Newport
— 7 nights
Drive
8
Aquinnah, Martha's Vineyard
— 1 night
Unknown
9
Nantucket
— 5 nights
Ferry to Hyannis, MA, Taxi to Provincetown
10
Provincetown
— 4 nights
Drive
11
Sandwich
— 5 nights
Drive
12
Boston
— 7 nights
Fly

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Bar Harbor, Mount Desert Island

— 5 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Somesville Historical Museum and Gardens and Whopaints Gallery will appeal to museum buffs. Discover out-of-the-way places like Kayaking & Canoeing and Egg Rock Light. Get out of town with these interesting Bar Harbor side-trips: Ship Harbor Nature Trail (in Bass Harbor) and Wonderland Trail (in Southwest Harbor). There's lots more to do: trek along Bar Island Trails, explore the striking landscape at Otter Cliff, explore the landscape on two wheels at Carriage Roads, and contemplate the waterfront views at Frenchman Bay.

For reviews, photos, traveler tips, and more tourist information, refer to the Bar Harbor online route planner.

Boston to Bar Harbor is an approximately 5-hour flight. You can also fly; or drive; or take a bus. In May, Bar Harbor is little chillier than Boston - with highs of 18°C and lows of 7°C. Finish your sightseeing early on the 5th (Sat) to allow enough time to drive to Rockland.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips

Rockland

— 3 nights
Rockland is a city in Knox County, Maine, in the United States. Do some cultural sightseeing at Pemaquid Point Lighthouse and Owls Head Transportation Museum. Get in touch with nature at Colonial Pemaquid State Historic Site and Camden Hills State Park. Venture out of the city with trips to Marshall Point Lighthouse Museum (in Port Clyde), Sweetgrass Farm Winery and Distillery (in Union) and The Wilson Memorial Chapel (in East Boothbay). It doesn't end there: explore the galleries of Farnsworth Art Museum and visit a coastal fixture at Rockland Breakwater Light.

For maps, reviews, other places to visit, and other tourist information, use the Rockland trip planner.

Getting from Bar Harbor to Rockland by car takes about 2.5 hours. Other options: take a bus. In June in Rockland, expect temperatures between 23°C during the day and 12°C at night. Finish your sightseeing early on the 8th (Tue) to allow enough time to drive to Portland.

Things to do in Rockland

Historic Sites · Museums · Nature · Parks

Side Trips

Portland

— 6 nights

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.
Step off the beaten path and head to Strawbery Banke Museum and Eastern Promenade Trail. Museum-lovers will get to explore Maine State Museum and Maine Maritime Museum. Change things up with these side-trips from Portland: Wells (Wells Beach & Rachel Carson National Wildlife Refuge), Mount Agamenticus (in York) and Ogunquit (Marginal Way Walkway & Ogunquit Museum of American Art). And it doesn't end there: learn insider's secrets on The Maine Brew Bus, see what you can catch with a fishing tour, visit a coastal fixture at Portland Breakwater Lighthouse, and get engrossed in the history at Victoria Mansion.

To see traveler tips, reviews, more things to do, and tourist information, use the Portland trip itinerary planning site.

Drive from Rockland to Portland in 2 hours. Alternatively, you can take a bus. In June, daytime highs in Portland are 26°C, while nighttime lows are 14°C. Cap off your sightseeing on the 14th (Mon) early enough to go by car to North Conway.

Things to do in Portland

Outdoors · Historic Sites · Museums · Parks

Side Trips

North Conway

— 5 nights
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Explore hidden gems such as The Basin at Franconia Notch State Park and White Mountain National Forest. Let the collections at Wright Museum of WWII and Mount Washington Observatory Weather Discovery Center capture your imagination. You'll find plenty of places to visit near North Conway: Pemi Valley Moose Tours (in Lincoln), Franconia Notch State Park (in Franconia) and Polar Caves Park (in Rumney). And it doesn't end there: take your sightseeing to a higher altitude at West Rattlesnake Mountain, find something for the whole family at Story Land, glide through natural beauty at Great Glen Trails Outdoor Center, and pause for some serene contemplation at The Little White Church.

For reviews, where to stay, maps, and other tourist information, use the North Conway journey planning tool.

You can drive from Portland to North Conway in 2 hours. Another option is to do a combination of bus and taxi. In June in North Conway, expect temperatures between 28°C during the day and 17°C at night. Finish your sightseeing early on the 19th (Sat) so you can drive to Bennington.

Things to do in North Conway

Parks · Nature · Outdoors · Tours

Side Trips

Bennington

— 3 nights
Bennington is a town in Bennington County, Vermont, in the United States. Satisfy your inner culture vulture at MASS MoCA and Shelburne Falls Trolley Museum. Step out of the city life by going to Zipline and Monument Mountain. Get out of town with these interesting Bennington side-trips: Historic Deerfield (in Deerfield), Pittsfield (Hancock Shaker Village & Balderdash Cellars) and National Shrine of the Divine Mercy (in Stockbridge). There's still lots to do: look for gifts at Ozzie's Glass Gallery.

To see reviews, where to stay, other places to visit, and other tourist information, use the Bennington journey planner.

You can drive from North Conway to Bennington in 4.5 hours. Other options are to take a bus; or do a combination of bus and train. Traveling from North Conway in June, you can expect nighttime temperatures to be slightly colder in Bennington, with lows of 13°C. Wrap up your sightseeing on the 22nd (Tue) early enough to travel to Groton.

Things to do in Bennington

Museums · Historic Sites · Outdoors · Tours

Side Trips

Groton

— 5 nights
Groton is a town located on the Thames River in New London County, Connecticut, United States. Deepen your sense of the past at sights like Florence Griswold Museum and Watch Hill Lighthouse. Explore hidden gems such as The Submarine Force Museum and New Britain Museum of American Art. Get out of town with these interesting Groton side-trips: Dinosaur State Park (in Rocky Hill), Gillette Castle State Park (in East Haddam) and Hartford (Harriet Beecher Stowe Center, The Mark Twain House & Museum, &more). The adventure continues: admire the majestic nature at Fort Trumbull State Park, explore the different monuments and memorials at Elm Grove Cemetery, snap pictures at Old Drake Hill Flower Bridge, and go for a walk through Mystic River Historical Society.

To find where to stay, photos, traveler tips, and more tourist information, read our Groton trip planner.

Getting from Bennington to Groton by car takes about 3 hours. In June in Groton, expect temperatures between 27°C during the day and 17°C at night. Finish your sightseeing early on the 27th (Sun) to allow enough time to drive to Newport.

Things to do in Groton

Museums · Historic Sites · Nature · Parks

Side Trips

Newport

— 7 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Museum-lovers will get to explore The Breakers and RISD Museum. Cliff Walk and Lizzie Borden House are good opportunities to explore the local culture. Venture out of the city with trips to Museum of Madeirian Heritage (in New Bedford), Chatham Marconi Maritime Center (in North Chatham) and Battleship Cove (in Fall River). The adventure continues: examine the collection at Newport Car Museum, browse the exhibits of International Tennis Hall of Fame, steep yourself in history at Chateau-sur-Mer, and enjoy the sea views from Beavertail Lighthouse and Park.

Before you visit Newport, use our trip planner to discover what you can do and see there.

You can drive from Groton to Newport in 1.5 hours. In June, daytime highs in Newport are 26°C, while nighttime lows are 17°C. Finish your sightseeing early on the 4th (Sun) to allow enough time to drive to Aquinnah.

Things to do in Newport

Historic Sites · Museums · Parks · Outdoors

Side Trips

Aquinnah, Martha's Vineyard

— 1 night
Aquinnah is a town located on the island of Martha's Vineyard in Massachusetts. On the 5th (Mon), kick back and relax at Menemsha Hills, explore the striking landscape at Aquinnah Cliffs, then visit a coastal fixture at Gay Head Lighthouse, and finally enjoy the sand and surf at Menemsha Public Beach.

To find ratings, maps, and other tourist information, go to the Aquinnah trip website.

Drive from Newport to Aquinnah in 3.5 hours. In July, plan for daily highs up to 30°C, and evening lows to 20°C. Finish your sightseeing early on the 5th (Mon) to allow enough time to travel to Nantucket.

Things to do in Aquinnah

Parks · Beaches · Outdoors · Historic Sites

Side Trips

Nantucket

— 5 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Do some cultural sightseeing at Brant Point Lighthouse and Great Point Light. Get in touch with nature at Madaket Beach and Jetties Beach. And it doesn't end there: visit a coastal fixture at Sankaty Head Lighthouse, sample the fine beverages at Cisco Brewers, appreciate the extensive heritage of Milestone Bog, and see the interesting displays at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

To find maps, more things to do, photos, and tourist information, you can read our Nantucket trip itinerary builder tool.

You can travel from Aquinnah to Nantucket in 3 hours. In July, daytime highs in Nantucket are 28°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 10th (Sat) early enough to travel to Provincetown.

Things to do in Nantucket

Historic Sites · Outdoors · Parks · Beaches

Provincetown

— 4 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Wellfleet Bay Wildlife Sanctuary and Salt Pond Visitor Center are good opportunities to explore the local culture. You'll discover tucked-away gems like Art's Dune Tours and Nauset Lighthouse. Venture out of the city with trips to Chatham Lighthouse (in Chatham), First Encounter Beach (in Eastham) and Orleans (Nauset Beach & Skaket Beach). There's much more to do: hike along Cape Cod Provincelands Trail, see the interesting displays at Pilgrim Monument & Provincetown Museum, do a tasting at Truro Vineyards of Cape Cod, and stroll through Marconi Beach.

For more things to do, photos, ratings, and more tourist information, use the Provincetown day trip website.

You can do a combination of ferry and taxi from Nantucket to Provincetown in 3 hours. Another option is to do a combination of ferry and bus. In July, daytime highs in Provincetown are 30°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 14th (Wed) to allow time to drive to Sandwich.

Things to do in Provincetown

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Sandwich

— 5 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Eschew the tourist crowds and head to Heritage Museums & Gardens and Sandwich Glass Museum. Get some cultural insight at New Bedford Whaling Museum and National Monument to the Forefathers. You'll find plenty of places to visit near Sandwich: Edgartown Lighthouse (in Edgartown), Oak Bluffs (Martha's Vineyard Camp meeting Association (MVCMA) & Island Alpaca Company of Martha's Vineyard) and Nobska Point Lighthouse (in Woods Hole). The adventure continues: get engrossed in the history at The Jenney, make a trip to Plymouth Rock, contemplate the long history of Hoxie House, and gain insight at Mayflower II.

To see more things to do, traveler tips, and other tourist information, use the Sandwich trip itinerary maker app.

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. In July, daily temperatures in Sandwich can reach 31°C, while at night they dip to 20°C. Finish up your sightseeing early on the 19th (Mon) so you can go by car to Boston.

Things to do in Sandwich

Museums · Historic Sites · Outdoors · Tours

Side Trips

Boston

— 7 nights

Beantown

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.
Old State House and Edward M. Kennedy Institute for the United States Senate will appeal to museum buffs. Step out of the city life by going to Adams National Historical Park and Castle Island. Get out of town with these interesting Boston side-trips: Lexington Green (in Lexington), Gloucester (The Cultural Center at Rocky Neck & Good Harbor Beach) and Concord (Louisa May Alcott's Orchard House, Minuteman National Park - Old North Bridge, &more). The adventure continues: contemplate the long history of Hancock-Clarke House, admire the landmark architecture of Trinity Church, take an in-depth tour of Buckman Tavern, and explore the world behind art at Harvard Art Museums.

To find traveler tips, reviews, where to stay, and more tourist information, go to the Boston trip maker site.

You can drive from Sandwich to Boston in 1.5 hours. Another option is to take a bus. In July in Boston, expect temperatures between 33°C during the day and 22°C at night. On the 26th (Mon), you'll have the morning to explore before heading back home.

Things to do in Boston

Historic Sites · Parks · Museums · Nature

Side Trips