15 days in New England Itinerary

15 days in New England Itinerary

Created using Inspirock New England route maker

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Route & dates

15 days in New England Itinerary

Start: Cleveland
Fly:  4​h
1
Boston
— 3 nights
Drive:  1​h 30​min
2
Ogunquit
— 1 night
Drive:  2​h 30​min
3
Camden
— 2 nights
Drive:  1​h 45​min
4
Bar Harbor, Mount Desert Island
— 3 nights
Fly:  5​h 30​min
5
Provincetown
— 2 nights
Drive:  2​h 45​min
6
Newport
— 2 nights
Bus + Fly:  6​h 15​min
End: Cleveland

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.
Head to Newbury Street and Quincy Marketfor plenty of shopping. Step out of the city life by going to Halibut Point State Park and Minute Man National Historical Park. Take a break from Boston with a short trip to Good Harbor Beach in Gloucester, about 1h 05 min away. And it doesn't end there: explore the world behind art at Museum of Fine Arts, wander the streets of Waterfront, steep yourself in history at The Paul Revere House, and get engrossed in the history at Buckman Tavern.

For maps, photos, reviews, and tourist information, read Boston trip itinerary maker .

Cleveland to Boston is an approximately 4-hour flight. You can also drive; or take a bus. In September, daily temperatures in Boston can reach 75°F, while at night they dip to 59°F. Finish up your sightseeing early on the 30th (Mon) so you can go by car to Ogunquit.

Things to do in Boston

Parks Neighborhoods Nature

Side Trips

Minute Man National Historical Park, Good Harbor Beach, Buckman Tavern, Halibut Point State Park
Highlights from your plan
Minute Man National Historical Park ©
Halibut Point State Park ©
Halibut Point State Park
Good Harbor Beach ©
Good Harbor Beach

1
night
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.
Kick off your visit on the 1st (Tue): stroll through Ogunquit Beach, then take in the dramatic natural features at Perkins Cove, and then get to know the fascinating history of Marginal Way Walkway.

To find traveler tips, more things to do, and more tourist information, read our Ogunquit day trip planning website .

You can drive from Boston to Ogunquit in 1.5 hours. Other options are to take a train; or take a bus. Traveling from Boston in September, Ogunquit is slightly colder at night with lows of 48°F. Cap off your sightseeing on the 1st (Tue) early enough to go by car to Camden.

Things to do in Ogunquit

Parks Beaches Outdoors
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Ogunquit Beach ©
Ogunquit Beach
Perkins Cove ©
Perkins Cove

2
nights
Camden

Camden ©
Camden is a town in Knox County, Maine, United States. On the 2nd (Wed), stop by Maine State Prison Store, take in the awesome beauty at Mount Battie, and then immerse yourself in nature at Camden Hills State Park. Keep things going the next day: enjoy the sand and surf at Shirttail Point, walk around Camden Harbor Park and Amphitheatre, do a tasting at Cellardoor Winery, then make a trip to Curtis Island Light, and finally learn about winemaking at Sweetgrass Winery and Distillery.

To see photos, where to stay, maps, and other tourist information, go to the Camden holiday site .

Traveling by car from Ogunquit to Camden takes 2.5 hours. Alternatively, you can do a combination of train and bus; or do a combination of bus and flight. In October, plan for daily highs up to 58°F, and evening lows to 42°F. Cap off your sightseeing on the 3rd (Thu) early enough to go by car to Bar Harbor.

Things to do in Camden

Parks Nature Beaches

Side Trips

Maine State Prison Store, Sweetgrass Winery and Distillery, Cellardoor Winery
Highlights from your plan
Maine State Prison Store ©
Maine State Prison Store
Cellardoor Winery ©
Cellardoor Winery
Camden Hills State Park ©
Camden Hills State Park

3
nights
Bar Harbor, Mount Desert Island

Bar Harbor
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Step off the beaten path and head to Acadia National Park and Egg Rock Light. Get outdoors at Mount Desert Island and Shore Path. There's lots more to do: look for gifts at Fiore Artisan Olive Oils and Vinegars, sample the tasty concoctions at Atlantic Brewing Company, stroll around Agamont Park, and admire the natural beauty at Asticou Terraces / Thuya Garden.

To find reviews, where to stay, traveler tips, and tourist information, refer to the Bar Harbor vacation planning app .

Traveling by car from Camden to Bar Harbor takes 2 hours. Alternatively, you can take a bus. October in Bar Harbor sees daily highs of 59°F and lows of 42°F at night. Cap off your sightseeing on the 6th (Sun) early enough to travel to Provincetown.

Things to do in Bar Harbor

Parks Wildlife Breweries & Distilleries

Side Trip

Asticou Terraces / Thuya Garden
Highlights from your plan
Asticou Terraces / Thuya Garden
Asticou Terraces / Thuya Garden
Egg Rock Light ©
Egg Rock Light
Atlantic Brewing Company ©
Atlantic Brewing Company

2
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.
You'll enjoy a bit of beach vacationing at Herring Cove Beach and Nauset Light Beach. Get a sense of the local culture at Pilgrim Monument & Provincetown Museum and Provincetown Town Hall. There's much more to do: enjoy the sand and surf at Long Point, get lost in a book at Provincetown Library, take a leisurely stroll along MacMillan Wharf, and get to know the fascinating history of Wellfleet Bay Wildlife Sanctuary.

To find other places to visit, traveler tips, where to stay, and more tourist information, refer to the Provincetown trip itinerary tool .

Getting from Bar Harbor to Provincetown by flight takes about 5.5 hours. Other options: drive; or do a combination of bus and ferry. Traveling from Bar Harbor in October, Provincetown is a bit warmer at night with lows of 49°F. Finish your sightseeing early on the 9th (Wed) to allow enough time to drive to Newport.

Things to do in Provincetown

Parks Outdoors Wildlife

Side Trips

Nauset Light Beach, Wellfleet Bay Wildlife Sanctuary
Highlights from your plan
Beech Forest, Provincetown ©
Beech Forest, Provincetown
Herring Cove Beach ©
Herring Cove Beach
Long Point ©
Long Point

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 10th (Thu): make a trip to Cliff Walk, examine the collection at The Breakers, then cruise along Ocean Drive Historic District, and finally take in the exciting artwork at Thames Glass. On your second day here, kick back and relax at Sachuest Beach (Second Beach), then explore the world behind art at National Museum of American Illustration, and then steep yourself in history at Chateau-sur-Mer.

To find maps, reviews, ratings, and other tourist information, you can read our Newport online route planner .

Traveling by car from Provincetown to Newport takes 3 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of ferry and train. In October, daytime highs in Newport are 64°F, while nighttime lows are 50°F. Cap off your sightseeing on the 11th (Fri) early enough to travel back home.

Things to do in Newport

Outdoors Historic Sites Parks

Side Trip

Sachuest Beach (Second Beach)
Highlights from your plan
Chateau-sur-Mer ©
Chateau-sur-Mer
The Breakers ©
The Breakers

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