19 days in New England Itinerary

19 days in New England Itinerary

Created using Inspirock New England trip itinerary planner

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Route & dates

19 days in New England Itinerary

Start: New York City
Drive:  4​h
1
Boston
— 3 nights
Drive:  5​h 15​min
2
Bar Harbor, Mount Desert Island
— 4 nights
Drive:  4​h
3
Ogunquit
— 3 nights
Drive:  3​h
4
Newport
— 2 nights
Drive:  1​h 15​min
5
Sandwich
— 2 nights
Drive:  1​h 15​min
6
Provincetown
— 3 nights
Fly:  5​h 15​min
End: New York City

3
nights
Boston

Boston ©
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.
Get in touch with nature at Dolphin & Whale Watching and Walden Pond State Reservation. Museum of Fine Arts and Louisa May Alcott's Orchard House will appeal to museum buffs. Take a break from Boston with a short trip to The House of the Seven Gables in Salem, about 42 minutes away. Next up on the itinerary: buy something for everyone on your list at Faneuil Hall Marketplace, get to know the fascinating history of Freedom Trail, admire all the interesting features of Fenway Park, and take in nature's colorful creations at Boston Public Garden.

For other places to visit, more things to do, maps, and more tourist information, read our Boston trip website .

New York City to Boston is an approximately 3-hour combination of bus and flight. You can also fly; or drive. Traveling from New York City in October, expect Boston to be little chillier, temps between 20°C and 11°C. Finish your sightseeing early on the 5th (Sat) so you can travel to Bar Harbor.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Concord, Brookline Booksmith, Dolphin & Whale Watching, The House of the Seven Gables
Highlights from your plan
Freedom Trail ©
Freedom Trail
Museum of Fine Arts ©
Museum of Fine Arts
Louisa May Alcott's Orchard House ©

4
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. The Seal Cove Auto Museum and Bass Harbor Head Lighthouse are good opportunities to explore the local culture. Escape the urban bustle at Acadia National Park and Cadillac Mountain. There's much more to do: head off the coast to Mount Desert Island, kick back and relax at Sand Beach, take in the spiritual surroundings of St. Saviour's Church :, and look for all kinds of wild species at Shore Path.

To find traveler tips, reviews, maps, and other tourist information, refer to the Bar Harbor travel planner .

Traveling by flight from Boston to Bar Harbor takes 4.5 hours. Alternatively, you can do a combination of flight and car; or drive. Prepare for slightly colder weather when traveling from Boston in October: high temperatures in Bar Harbor hover around 17°C and lows are around 6°C. Wrap up your sightseeing on the 9th (Wed) to allow time to drive to Ogunquit.

Things to do in Bar Harbor

Parks Nature Outdoors

Side Trips

Acadia National Park, Bass Harbor Head Lighthouse, The Seal Cove Auto Museum
Highlights from your plan
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Cadillac Mountain ©
Cadillac Mountain
Shore Path ©
Shore Path

3
nights
Ogunquit

Ogunquit ©
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.
Step out of the city life by going to Ogunquit Beach and Perkins Cove. Appreciate the collections at Portland Head Light and Wright Museum of WWII. Explore Ogunquit's surroundings by going to Just Us Chickens Gallery (in Kittery), Maine Art Hill (in Kennebunk) and Kennebunkport (W. Robert Paine Gallery & Mast Cove Galleries). There's lots more to do: get to know the fascinating history of Marginal Way Walkway, get a taste of the local shopping with Abacus, and enjoy the sea views from Cape Neddick Nubble Lighthouse.

For other places to visit, traveler tips, and more tourist information, use the Ogunquit tour planner .

Drive from Bar Harbor to Ogunquit in 4 hours. Alternatively, you can do a combination of flight and bus; or take a bus. Expect a daytime high around 19°C in October, and nighttime lows around 3°C. Cap off your sightseeing on the 12th (Sat) early enough to go by car to Newport.

Things to do in Ogunquit

Museums Shopping Parks

Side Trips

Kennebunkport, Nubble Lighthouse, Wright Museum of WWII, Maine Art Hill, Just Us Chickens Gallery
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portland Head Light ©
Portland Head Light
Wright Museum of WWII ©
Wright Museum of WWII

2
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 13th (Sun): examine the collection at The Breakers, then admire all the interesting features of Cliff Walk, then look for gifts at Thames Glass, and finally admire all the interesting features of Ocean Drive Historic District. Get ready for a full day of sightseeing on the next day: enjoy the sea views from Beavertail Lighthouse and Park, get a taste of the local shopping with The Glass Station, then take an in-depth tour of Lizzie Borden House, and finally view the masterpieces at Arthur Moniz Art Gallery.

For reviews, photos, maps, and tourist information, use the Newport trip planner.

Traveling by car from Ogunquit to Newport takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect somewhat warmer evenings in Newport when traveling from Ogunquit in October, with lows around 11°C. Finish your sightseeing early on the 14th (Mon) so you can drive to Sandwich.

Things to do in Newport

Historic Sites Museums Parks

Side Trips

Lizzie Borden House, Arthur Moniz Art Gallery, The Glass Station, Beavertail Lighthouse and Park
Highlights from your plan
Beavertail Lighthouse and Park ©
Beavertail Lighthouse and Park
Lizzie Borden House ©
Lizzie Borden House
The Breakers ©
The Breakers

2
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. On the 15th (Tue), get curious at Sandwich Glass Museum, then examine the collection at Heritage Museums & Gardens, then explore and take pictures at Highfield Hall & Gardens, and finally explore the landscape on two wheels at Shining Sea Bikeway. On the next day, take in the exciting artwork at McDermott Glass Studio, brush up on your military savvy at Cape Cod Maritime Museum, take in the exciting artwork at Samuell Day Gallery, then steep yourself in history at Edward Gorey House, and finally kick back and relax at Chatham Lighthouse Beach.

To find other places to visit, maps, traveler tips, and more tourist information, go to the Sandwich online trip itinerary builder .

Getting from Newport to Sandwich by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and train. In October, daily temperatures in Sandwich can reach 20°C, while at night they dip to 9°C. Finish your sightseeing early on the 16th (Wed) so you can drive to Provincetown.

Things to do in Sandwich

Museums Parks Outdoors

Side Trips

Falmouth, Samuell Day Gallery, Edward Gorey House, Cape Cod Maritime Museum, Chatham Lighthouse Beach
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Edward Gorey House ©
Edward Gorey House
Sandwich Glass Museum ©
Sandwich Glass Museum

3
nights
Provincetown

Provincetown ©
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.
Satisfy your inner culture vulture at Pilgrim Monument & Provincetown Museum and Captain Penniman House. You'll get in some beach time at Cape Cod National Seashore and Race Point Beach. The adventure continues: kick back and relax at Herring Cove Beach, take a leisurely stroll along MacMillan Wharf, appreciate the extensive heritage of Wellfleet Bay Wildlife Sanctuary, and don't miss a visit to Commercial Street.

To find reviews, where to stay, traveler tips, and tourist information, read our Provincetown road trip tool .

Drive from Sandwich to Provincetown in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 20°C in October, and nighttime lows around 11°C. Cap off your sightseeing on the 19th (Sat) early enough to travel back home.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Captain Penniman House, Cape Cod National Seashore, Wellfleet Bay Wildlife Sanctuary
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach
Herring Cove Beach ©
Herring Cove Beach

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