53 days in New England Itinerary

53 days in New England Itinerary

Created using Inspirock New England sightseeing planner
Make it your trip
Fly to Bradley International Airport, Drive to Pittsfield
1
Pittsfield
— 2 nights
Drive
2
Boston
— 2 nights
Fly
3
Nantucket
— 2 nights
Ferry to Hyannis, MA, Taxi to Dennis
4
Dennis
— 3 nights
Drive
5
Newport
— 2 nights
Fly
6
Bar Harbor, Mount Desert Island
— 3 nights
Drive
7
Rockland
— 2 nights
Drive
8
Portland
— 33 nights
Drive
9
Lincoln
— 3 nights
Fly

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Pittsfield — 2 nights

Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Do some cultural sightseeing at The Mount, Edith Wharton's Home and Herman Melville's Arrowhead. Step out of the city life by going to Pleasant Valley Sanctuary and Pittsfield State Forest. Step out of Pittsfield to go to Sheffield and see Berkshire Mountain Distillers, which is approximately 50 minutes away. The adventure continues: admire the landmark architecture of Ventfort Hall Mansion and Gilded Age Museum, explore the world behind art at Norman Rockwell Museum, see the interesting displays at Frelinghuysen Morris House & Studio, and view the masterpieces at Ozzie's Glass Gallery.

For other places to visit, where to stay, photos, and more tourist information, go to the Pittsfield tour planner.

Tallahassee to Pittsfield is an approximately 8-hour combination of flight and car. You can also drive. Plan for a bit cooler temperatures traveling from Tallahassee in July, with highs in Pittsfield at 79°F and lows at 59°F. Wrap up your sightseeing on the 3rd (Mon) early enough to drive to Boston.
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Museums · Parks · Historic Sites · Nature
Side Trips
Find places to stay Jul 1 — 3:
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Boston — 2 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.
Kick off your visit on the 4th (Tue): see the interesting displays at The Mapparium, then stop by Back Bay, then explore the landscape on two wheels at Charles River Bike Path, and finally ponder the world of politics at Old State House. On the next day, browse the exhibits of Hancock-Clarke House, then take an in-depth tour of Louisa May Alcott's Orchard House, then steep yourself in history at Buckman Tavern, and finally get to know the fascinating history of HarborWalk.

To find maps, ratings, photos, and tourist information, you can read our Boston trip planner.

Traveling by car from Pittsfield to Boston takes 2.5 hours. Plan for a bit warmer nights when traveling from Pittsfield in July since evenings lows in Boston dip to 67°F. Finish up your sightseeing early on the 5th (Wed) so you can catch the flight to Nantucket.
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Museums · Historic Sites · Trails · Parks
Side Trips
Find places to stay Jul 3 — 5:
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Nantucket — 2 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 6th (Thu): make a trip to St Paul's Episcopal Church, steep yourself in history at Quaker Meeting House, then engage your brain at Maria Mitchell Association, then see the interesting displays at Nantucket Lightship Basket Museum, and finally enjoy the sand and surf at Nobadeer. Get ready for a full day of sightseeing on the next day: contemplate the long history of Fire Hose Cart House, then contemplate the long history of Greater Light, and then sample the tasty concoctions at Cisco Brewers.

To see traveler tips, photos, where to stay, and other tourist information, go to the Nantucket trip builder site.

Traveling by flight from Boston to Nantucket takes 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. When traveling from Boston in July, plan for a bit cooler days and about the same nights in Nantucket: temperatures range from 76°F by day to 64°F at night. Finish your sightseeing early on the 7th (Fri) to allow enough time to travel to Dennis.
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Historic Sites · Breweries & Distilleries · Wineries · Museums
Find places to stay Jul 5 — 7:
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Dennis — 3 nights

Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. Your inner history buff will appreciate Marconi-RCA Wireless Museum and Chatham's Godfrey Windmill. You'll explore the less-touristy side of things at Mayflower Beach and Harding Beach. Change things up with a short trip to Boat Tours & Water Sports in Chatham (about 30 minutes away). There's still lots to do: kick back and relax at Corporation Beach, stroll through West Dennis Beach, see the interesting displays at Shark Center, and stop by Chatham Candy Manor.

To see maps, other places to visit, where to stay, and tourist information, go to the Dennis online tour builder.

Do a combination of ferry and taxi from Nantucket to Dennis in 2 hours. Alternatively, you can fly. In July, daytime highs in Dennis are 80°F, while nighttime lows are 66°F. Wrap up your sightseeing on the 10th (Mon) early enough to drive to Newport.
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Outdoors · Parks · Beaches · Historic Sites
Side Trips
Find places to stay Jul 7 — 10:
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Newport — 2 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
On the 11th (Tue), examine the collection at Audrain Automobile Museum, contemplate in the serene atmosphere at Touro Synagogue, then don't miss a visit to Bellevue Avenue Historic District, and finally explore the striking landscape at Purgatory Chasm. On the 12th (Wed), you'll have a packed day of sightseeing: examine the collection at International Tennis Hall of Fame, then take in the architecture and atmosphere at St. Mary's Catholic Church, then get a new perspective on things with Fish'n Tales Adventures, and finally see the interesting displays at Newport Car Museum.

For maps, reviews, traveler tips, and more tourist information, read our Newport holiday planning site.

Drive from Dennis to Newport in 2 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi, bus, and train. In July, daytime highs in Newport are 80°F, while nighttime lows are 66°F. Finish your sightseeing early on the 12th (Wed) to allow enough time to fly to Bar Harbor.
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Museums · Outdoors · Historic Sites · Scenic Drive
Side Trips
Find places to stay Jul 10 — 12:
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Bar Harbor, Mount Desert Island — 3 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. George B. Dorr Museum of Natural History and Little Village Gifts will appeal to museum buffs. Discover out-of-the-way places like Cadillac Mountain North Ridge Trail and Nature & Wildlife Tours. The adventure continues: take a tour by water with Boat Tours & Water Sports, take in the awesome beauty at Cadillac Mountain, sample some tasty brews at Maine Foodie Tours, and look for all kinds of wild species at Shore Path.

To find where to stay, maps, ratings, and other tourist information, use the Bar Harbor itinerary planner.

You can fly from Newport to Bar Harbor in 3 hours. Alternatively, you can drive; or take a bus. Plan for little chillier temperatures traveling from Newport in July, with highs in Bar Harbor at 75°F and lows at 58°F. Finish your sightseeing early on the 15th (Sat) so you can drive to Rockland.
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Tours · Outdoors · Parks · Wildlife
Side Trip
Find places to stay Jul 12 — 15:
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Rockland — 2 nights

Rockland is a city in Knox County, Maine, in the United States. Start off your visit on the 16th (Sun): identify plant and animal life at Beech Hill Reserve, learn about winemaking at Sweetgrass Farm Winery and Distillery, then look for gifts at Maine State Prison Store, and finally steep yourself in history at General Henry Knox Museum / Montpelier. Keep things going the next day: see the interesting displays at Project Puffin Visitor Center, then enjoy the sea views from Maine Lighthouse Museum, then do a tasting at Breakwater Vineyards, and finally immerse yourself in nature at Owl's Head State Park.

To find reviews, ratings, where to stay, and tourist information, read our Rockland driving holiday planning site.

Drive from Bar Harbor to Rockland in 2.5 hours. Alternatively, you can take a bus. July in Rockland sees daily highs of 74°F and lows of 58°F at night. Cap off your sightseeing on the 17th (Mon) early enough to go by car to Portland.
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Museums · Parks · Historic Sites · Wineries
Side Trips
Find places to stay Jul 15 — 17:
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Portland — 33 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.
Museum-lovers will appreciate Victoria Mansion and Ogunquit Museum of American Art. Popular historic sites such as Marginal Way Walkway and Spring Point Ledge Lighthouse are in your itinerary. Change things up with these side-trips from Portland: Brunswick (Peary-MacMillan Arctic Museum, Joshua L. Chamberlain Museum, &more), Cliff Trail (in Harpswell) and Ogunquit (Perkins Cove, Ogunquit Beach, &more). There's much more to do: tour the pleasant surroundings at Wells Beach, sample the tasty concoctions at Allagash Brewing Company, don't miss a visit to St. Anthony's Monastery, and trek along Giant's Stairs Trail.

To find reviews, ratings, other places to visit, and more tourist information, go to the Portland road trip planning website.

Traveling by car from Rockland to Portland takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In July, daytime highs in Portland are 79°F, while nighttime lows are 61°F. Wrap up your sightseeing on the 19th (Sat) early enough to drive to Lincoln.
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Parks · Outdoors · Museums · Beaches
Side Trips
Find places to stay Jul 17 — Aug 19:
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Lincoln — 3 nights

Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Your inner history buff will appreciate The Frost Place and Flume Gorge. Visiting Echo Lake Beach and Mount Lafayette will get you outdoors. The adventure continues: learn about winemaking at Seven Birches Winery, take in the dramatic scenery at Georgiana Falls, tour the pleasant surroundings at Artist Bluff Trail, and contemplate the waterfront views at Profile Lake.

To see photos, more things to do, ratings, and tourist information, you can read our Lincoln online tour planner.

You can drive from Portland to Lincoln in 2.5 hours. Alternatively, you can take a bus. Expect slightly colder evenings in Lincoln when traveling from Portland in August, with lows around 54°F. Wrap up your sightseeing on the 22nd (Tue) early enough to fly back home.
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Parks · Nature · Outdoors · Historic Sites
Side Trips
Find places to stay Aug 19 — 22:
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