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 Bar Island Trails. Get out of town with these interesting Bar Harbor side-trips: Wonderland Trail (in Southwest Harbor) and Ship Harbor Nature Trail (in Bass Harbor). And it doesn't end there: enjoy the sea views from Egg Rock Light, kick back and relax at Sand Beach, explore the striking landscape at Thunder Hole, and hike along Ocean Path.

To see ratings, other places to visit, reviews, and other tourist information, refer to the Bar Harbor day trip website.

Boston to Bar Harbor is an approximately 5-hour flight. You can also fly; or drive; or take a bus. Traveling from Boston in May, expect Bar Harbor to be a bit cooler, temps between 18°C and 7°C. Cap off your sightseeing on the 5th (Sat) early enough to go by car 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 Colonial Pemaquid State Historic Site. Museum-lovers will get to explore Farnsworth Art Museum and Marshall Point Lighthouse Museum. You'll find plenty of places to visit near Rockland: Sweetgrass Farm Winery and Distillery (in Union) and The Wilson Memorial Chapel (in East Boothbay). And it doesn't end there: enjoy the sea views from Rockland Breakwater Light, admire the majestic nature at Camden Hills State Park, and see the interesting displays at Owls Head Transportation Museum.

For reviews, traveler tips, other places to visit, and other tourist information, go to the Rockland tour itinerary maker website.

Traveling by car from Bar Harbor to Rockland takes 2.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 23°C, and evening lows to 12°C. Wrap up your sightseeing on the 8th (Tue) early enough to drive to Portland.

Things to do in Rockland

Historic Sites · Museums · Parks · Nature

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 Ogunquit Museum of American Art. Change things up with these side-trips from Portland: Wells (Wells Beach & Rachel Carson National Wildlife Refuge), Marginal Way Walkway (in Ogunquit) and Maine Maritime Museum (in Bath). And it doesn't end there: explore the landscape on two wheels at Eastern Promenade Trail, visit a coastal fixture at Portland Breakwater Lighthouse, get engrossed in the history at Victoria Mansion, and sample some tasty brews at The Maine Brew Bus.

To see traveler tips, ratings, other places to visit, and other tourist information, refer to the Portland tour planner.

You can drive from Rockland to Portland in 2 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 26°C, and evening lows to 14°C. Wrap up your sightseeing on the 14th (Mon) early enough to drive 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: Franconia Notch State Park (in Franconia), Pemi Valley Moose Tours (in Lincoln) and Polar Caves Park (in Rumney). Next up on the itinerary: take in the dramatic natural features at Cathedral Ledge, glide through natural beauty at Great Glen Trails Outdoor Center, take in the dramatic scenery at Glen Ellis Falls, and take in the architecture and atmosphere at The Little White Church.

For photos, more things to do, maps, and other tourist information, you can read our North Conway trip planner.

Traveling by car from Portland to North Conway takes 2 hours. Alternatively, you can do a combination of bus and taxi. In June, daily temperatures in North Conway can reach 28°C, while at night they dip to 17°C. Finish up your sightseeing early on the 19th (Sat) so you can go by car 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 Historic Deerfield. Step out of the city life by going to Zipline and Monument Mountain. Get out of town with these interesting Bennington side-trips: National Shrine of the Divine Mercy (in Stockbridge), Pittsfield (Hancock Shaker Village & Balderdash Cellars) and Shelburne Falls Trolley Museum (in Shelburne Falls). 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 Fort Trumbull State Park. Get out of town with these interesting Groton side-trips: Dinosaur State Park (in Rocky Hill), New Britain Museum of American Art (in New Britain) and Gillette Castle State Park (in East Haddam). 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 · Parks · Nature

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 Fall River (Battleship Cove & Lizzie Borden House), Chatham Marconi Maritime Center (in North Chatham) and Museum of Madeirian Heritage (in New Bedford). The adventure continues: steep yourself in history at Fort Adams State Park, take in nature's colorful creations at Green Animals Topiary Gardens, contemplate in the serene atmosphere at Trinity Church, 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 · Outdoors · Beaches · 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 Sankaty Head Lighthouse. Get in touch with nature at Madaket Beach and Siasconset Beach. Next up on the itinerary: visit a coastal fixture at Great Point Light, make a trip to Old Mill, see the interesting displays at Whaling Museum, and do a tasting at Cisco Brewers.

To see traveler tips, ratings, photos, and more tourist information, you can read our Nantucket trip planner.

Travel from Aquinnah to Nantucket in 3 hours. July in Nantucket sees daily highs of 28°C and lows of 20°C at night. Finish up your sightseeing early on the 10th (Sat) so you can travel to Provincetown.

Things to do in Nantucket

Historic Sites · Parks · Outdoors · 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 Chatham Lighthouse are good opportunities to explore the local culture. You'll discover tucked-away gems like Art's Dune Tours and Herring Cove Beach. Venture out of the city with trips to Orleans (Nauset Beach & Skaket Beach) and Eastham (Salt Pond Visitor Center, Nauset Lighthouse, &more). There's much more to do: trek along Cape Cod Provincelands Trail, explore the world behind art at Provincetown Town Hall, kick back and relax at Marconi Beach, and do a tasting at Truro Vineyards of Cape Cod.

To see ratings, reviews, and other tourist information, read our Provincetown day trip planning site.

Traveling by combination of ferry and taxi from Nantucket to Provincetown takes 3 hours. Alternatively, you can 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) early enough 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 New Bedford Whaling Museum. Get some cultural insight at Sandwich Glass Museum and National Monument to the Forefathers. You'll find plenty of places to visit near Sandwich: Edgartown Lighthouse (in Edgartown), Nobska Point Lighthouse (in Woods Hole) and Oak Bluffs (Martha's Vineyard Camp meeting Association (MVCMA) & Island Alpaca Company of Martha's Vineyard). The adventure continues: get engrossed in the history at Pilgrim Hall Museum, 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). There's lots more to do: contemplate in the serene atmosphere at Trinity Church, steep yourself in history at Hancock-Clarke House, take a tour of Charlestown Navy Yard, and wander the streets of 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 · Parks · Museums · Nature

Side Trips