40 days in New England Itinerary

40 days in New England Itinerary

Created using Inspirock New England trip planner

Make it your trip
Fly
1
Boston
— 7 nights
Drive
2
Ogunquit
— 5 nights
Drive
3
Boothbay Harbor
— 5 nights
Drive
4
Bar Harbor, Mount Desert Island
— 5 nights
Fly
5
Newport
— 6 nights
Fly
6
Provincetown
— 6 nights
Drive
7
Sandwich
— 5 nights
Fly

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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.
Take a break from the city and head to Dolphin & Whale Watching and Gray's Beach. Your inner history buff will appreciate Freedom Trail and The House of the Seven Gables. You'll find plenty of places to visit near Boston: Salem (Peabody Essex Museum & Salem Witch Museum), Louisa May Alcott's Orchard House (in Concord) and Yarmouth Port (Captain Bangs Hallet House Museum & Edward Gorey House). There's much more to do: explore the world behind art at Museum of Fine Arts, stroll through Isabella Stewart Gardner Museum, get engrossed in the history at USS Constitution Museum, and shop like a local with Faneuil Hall Marketplace.

To find photos, other places to visit, more things to do, and other tourist information, read Boston road trip planning app.

Fresno to Boston is an approximately 10-hour flight. You can also drive; or do a combination of train and bus. The time zone difference when traveling from Fresno to Boston is 3 hours. Traveling from Fresno in September, things will get slightly colder in Boston: highs are around 75°F and lows about 59°F. Finish your sightseeing early on the 1st (Fri) to allow enough time to drive to Ogunquit.

Things to do in Boston

Museums · Historic Sites · Parks · Outdoors

Side Trips

Ogunquit

— 5 nights
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Escape the urban bustle at Kancamagus Highway and Boat Tours & Water Sports. Marginal Way Walkway and St. Ann's Episcopal Church will appeal to history buffs. Explore Ogunquit's surroundings by going to Portland Head Light (in Cape Elizabeth), The Little White Church (in Eaton) and Glen Ellis Falls (in Jackson). There's much more to do: explore the striking landscape at Perkins Cove, get engrossed in the history at Strawbery Banke Museum, take a peaceful walk through White Mountain National Forest, and tour the pleasant surroundings at Rachel Carson National Wildlife Refuge.

For more things to do, photos, reviews, and tourist information, use the Ogunquit day trip app.

Traveling by car from Boston to Ogunquit takes 1.5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Traveling from Boston in October, you can expect nighttime temperatures to be slightly colder in Ogunquit, with lows of 38°F. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Boothbay Harbor.

Things to do in Ogunquit

Historic Sites · Parks · Nature · Wildlife

Side Trips

Boothbay Harbor

— 5 nights
Boothbay Harbor is a town in Lincoln County, Maine, United States. Get in touch with nature at Cap'n Fish's Cruises and Coastal Maine Botanical Gardens. You'll explore and learn at Owls Head Transportation Museum and Colby College Museum of Art. Change things up with these side-trips from Boothbay Harbor: Mount Battie (in Camden), Farnsworth Art Museum (in Rockland) and Pemaquid Point Lighthouse (in Bristol). There's much more to do: see the interesting displays at Maine Maritime Museum, enjoy the sea views from Doubling Point Lighthouse, tour the pleasant surroundings at Boothbay Region Land Trust, and take in the architecture and atmosphere at The Wilson Memorial Chapel.

For photos, more things to do, other places to visit, and other tourist information, you can read our Boothbay Harbor trip website.

Getting from Ogunquit to Boothbay Harbor by car takes about 2 hours. Other options: do a combination of taxi and train; or do a combination of bus and taxi. In October in Boothbay Harbor, expect temperatures between 61°F during the day and 41°F at night. Finish your sightseeing early on the 11th (Mon) so you can drive to Bar Harbor.

Things to do in Boothbay Harbor

Museums · Parks · Wildlife · Historic Sites

Side Trips

Bar Harbor, Mount Desert Island

— 5 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Let the collections at The Seal Cove Auto Museum and Maine Granite Industry Museum capture your imagination. Get outdoors at Boat Tours & Water Sports and Schoodic Point. Next up on the itinerary: take in the awesome beauty at Cadillac Mountain, hike along Precipice Trail, explore and take pictures at Park Loop Road, and tour the pleasant surroundings at Shore Path.

For ratings, photos, traveler tips, and other tourist information, you can read our Bar Harbor travel site.

Traveling by car from Boothbay Harbor to Bar Harbor takes 3 hours. Alternatively, you can do a combination of taxi and bus. Expect a daytime high around 59°F in October, and nighttime lows around 42°F. Wrap up your sightseeing on the 16th (Sat) early enough to fly to Newport.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips

Newport

— 6 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Get some historical perspective at Cliff Walk and Lizzie Borden House. The Breakers and Thames Glass will appeal to museum buffs. Explore Newport's surroundings by going to Lippitt House Museum (in Providence), Chatham Marconi Maritime Center (in North Chatham) and Colt State Park (in Bristol). There's much more to do: take a memorable drive along Ocean Drive Historic District, examine the collection at Newport Car Museum, contemplate the long history of The Elms, and tour the old-fashioned way with a train tour.

To see more things to do, traveler tips, where to stay, and tourist information, read our Newport day trip planning app.

Fly from Bar Harbor to Newport in 3 hours. Alternatively, you can drive; or take a bus. Traveling from Bar Harbor in October, you can expect nighttime temperatures to be a bit warmer in Newport, with lows of 50°F. Wrap up your sightseeing on the 22nd (Fri) early enough to fly to Provincetown.

Things to do in Newport

Historic Sites · Museums · Tours · Outdoors

Side Trips

Provincetown

— 6 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.
Take a break from the city and head to Art's Dune Tours and Nauset Beach. Visit Atwood Museum and Captain Penniman House for their historical value. You'll find plenty of places to visit near Provincetown: Eastham (Coast Guard Beach, Salt Pond Visitor Center, &more) and Chatham (Chatham Lighthouse Beach & Chatham Railroad Museum). Next up on the itinerary: pause for some photo ops at Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Race Point Beach, tour the pleasant surroundings at Long Point, and take a leisurely stroll along MacMillan Wharf.

Find out how to plan Provincetown trip without stress by asking Inspirock to help create an itinerary.

You can fly from Newport to Provincetown in 2 hours. Alternatively, you can drive; or do a combination of bus and ferry. In October, plan for daily highs up to 63°F, and evening lows to 49°F. Wrap up your sightseeing on the 28th (Thu) to allow time to drive to Sandwich.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Sandwich

— 5 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Heritage Museums & Gardens and John F Kennedy Hyannis Museum will appeal to museum buffs. Get in touch with nature at Hyannis Whale Watcher Cruises and National Monument to the Forefathers. Explore Sandwich's surroundings by going to Falmouth (Highfield Hall & Gardens & Falmouth Museums on the Green), Woods Hole (Nobska Point Lighthouse & Woods Hole Oceanographic Institution) and Trinity Park Tabernacle (in Oak Bluffs). Next up on the itinerary: engage your brain at Sandwich Glass Museum, explore the activities along Cape Cod Canal, contemplate the long history of Plymouth Rock, and view the masterpieces at Samuell Day Gallery.

For where to stay, maps, reviews, and tourist information, read Sandwich trip itinerary planner.

You can drive from Provincetown to Sandwich in 1.5 hours. Another option is to take a bus. Expect a daytime high around 64°F in October, and nighttime lows around 46°F. Wrap up your sightseeing on the 2nd (Tue) early enough to fly back home.

Things to do in Sandwich

Museums · Historic Sites · Outdoors · Parks

Side Trips