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 Ship Harbor Nature Trail. When in Bar Harbor, make a side trip to see Wonderland Trail in Southwest Harbor, approximately Southwest Harbor away. There's lots more to do: enjoy the sea views from Egg Rock Light, explore the landscape on two wheels at Carriage Roads, tour the pleasant surroundings at Gorham Mountain Trail, and explore the striking landscape at Schoodic Peninsula.

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 The Wilson Memorial Chapel (in East Boothbay), Marshall Point Lighthouse Museum (in Port Clyde) and Sweetgrass Farm Winery and Distillery (in Union). 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 Fishing Charters & Tours. Museum-lovers will get to explore Maine State Museum and Maine Maritime Museum. Change things up with these side-trips from Portland: Ogunquit (Marginal Way Walkway & Ogunquit Museum of American Art), Wells (Wells Beach & Rachel Carson National Wildlife Refuge) and Mount Agamenticus (in York). And it doesn't end there: learn insider's secrets on The Maine Brew Bus, explore the landscape on two wheels at Eastern Promenade Trail, 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 Wright Museum of WWII. Mount Washington Observatory Weather Discovery Center and The Little White Church are good opportunities to explore the local culture. Get out of town with these interesting North Conway side-trips: Pemi Valley Moose Tours (in Lincoln), Franconia Notch State Park (in Franconia) and Polar Caves Park (in Rumney). The adventure continues: take in the dramatic natural features at Cathedral Ledge, hike along Rocky Gorge, get in on the family fun at Story Land, and take in the awesome beauty at West Rattlesnake Mountain.

To see ratings, where to stay, other places to visit, and more tourist information, read our North Conway trip site.

Drive from Portland to North Conway in 2 hours. Alternatively, you can do a combination of bus and taxi. June in North Conway sees daily highs of 28°C and lows of 17°C at night. Finish your sightseeing early on the 19th (Sat) to allow enough time to drive to Bennington.

Things to do in North Conway

Parks · Nature · Outdoors · Wildlife

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 · Adventure · Outdoors

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 Fort Trumbull State Park. Get out of town with these interesting Groton side-trips: Dinosaur State Park (in Rocky Hill), Gillette Castle State Park (in East Haddam) and New Britain Museum of American Art (in New Britain). The adventure continues: visit a coastal fixture at Stonington Lighthouse Museum, take in the pleasant sights at Mystic River Historical Society, steep yourself in history at The Mark Twain House & Museum, and stroll the grounds of Elm Grove Cemetery.

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 Rosecliff are good opportunities to explore the local culture. Venture out of the city with trips to Chatham Marconi Maritime Center (in North Chatham), Museum of Madeirian Heritage (in New Bedford) and Fall River (Battleship Cove & Lizzie Borden House). The adventure continues: examine the collection at Newport Car Museum, browse the exhibits of International Tennis Hall of Fame, steep yourself in history at Fort Adams State Park, 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 Chatham Lighthouse. Venture out of the city with trips to Orleans (Nauset Beach & Skaket Beach) and Eastham (Nauset Lighthouse & First Encounter 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

Outdoors · Parks · 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 New Bedford Whaling Museum. Get some cultural insight at Sandwich Glass Museum and The Jenney. You'll find plenty of places to visit near Sandwich: Oak Bluffs (Martha's Vineyard Camp meeting Association (MVCMA) & Island Alpaca Company of Martha's Vineyard), Edgartown Lighthouse (in Edgartown) and Nobska Point Lighthouse (in Woods Hole). And it doesn't end there: get engrossed in the history at Pilgrim Hall Museum, make a trip to Plymouth Rock, steep yourself in history at Hoxie House, and immerse yourself in nature at National Monument to the Forefathers.

Quickly create a custom-made itinerary for Sandwich using our trip planner.

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. In July, daytime highs in Sandwich are 31°C, while nighttime lows are 20°C. Finish your sightseeing early on the 19th (Mon) to allow enough time to drive to Boston.

Things to do in Sandwich

Museums · Historic Sites · Outdoors · Wildlife

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 Harvard Art Museums will appeal to museum buffs. Step out of the city life by going to Adams National Historical Park and Halibut Point State Park. Get out of town with these interesting Boston side-trips: Lexington Green (in Lexington), Concord (Louisa May Alcott's Orchard House, Minuteman National Park - Old North Bridge, &more) and Gloucester (The Cultural Center at Rocky Neck & Good Harbor Beach). There's lots more to do: contemplate in the serene atmosphere at Trinity Church, steep yourself in history at Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, appreciate the extensive heritage of HarborWalk, and visit Back Bay.

To find more things to do, ratings, and more tourist information, read our Boston online road trip planner.

You can drive from Sandwich to Boston in 1.5 hours. Another option is to take a bus. In July, daytime highs in Boston are 33°C, while nighttime lows are 22°C. You'll have a few hours on the 26th (Mon) to wrap things up before traveling home.

Things to do in Boston

Historic Sites · Museums · Parks · Nature

Side Trips