57 days in New England Itinerary

57 days in New England Itinerary

Created using Inspirock New England vacation planner

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Route & dates

57 days in New England Itinerary

Start: Fredericksburg
+2
Train + Subway + Fly:  5 h
1
Boston
— 9 nights
Bus:  1 h 45 min
2
Newport
— 7 nights
Drive:  1 h 30 min
3
Sandwich
— 6 nights
Drive:  1 h 15 min
4
Provincetown
— 6 nights
Drive:  3 h 15 min
5
Nantucket
— 7 nights
Fly:  5 h 30 min
6
Bar Harbor, Mount Desert Island
— 7 nights
Drive:  1 h 45 min
7
Camden
— 6 nights
Drive:  1 h 45 min
8
Portland
— 8 nights
Fly:  6 h 30 min
End: Knoxville

9
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.
Your itinerary includes some good beach time at Hampton Beach State Park and North Hampton State Beach. Deepen your sense of the past at sights like Freedom Trail and Old North Church & Historic Site. Venture out of the city with trips to Dolphin & Whale Watching (in Gloucester), Salem (The House of the Seven Gables, Salem Witch Museum, &more) and Crane Beach (in Ipswich). And it doesn't end there: explore the world behind art at Museum of Fine Arts, take a stroll through Newbury Street, take an in-depth tour of Boston Tea Party Ships & Museum, and walk around Boston Common.

To see where to stay, other places to visit, traveler tips, and more tourist information, read our Boston journey planner.

Fredericksburg to Boston is an approximately 5-hour flight. You can also do a combination of train and flight; or drive. When traveling from Fredericksburg in July, plan for a bit cooler days in Boston, with highs around 83°F, while nights are about the same with lows around 67°F. Wrap up your sightseeing on the 29th (Wed) early enough to take a bus to Newport.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Hampton Beach State Park, Woburn Public Library, Mount Auburn Cemetery, North Hampton State Beach
Highlights from your plan
North End ©
North End
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail

7
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Visit Misquamicut State Beach and Purgatory Chasm for some beach relaxation. Museum-lovers will get to explore The Breakers and National Museum of American Illustration. Explore Newport's surroundings by going to Mystic Seaport Museum (in Mystic) and Cottrell Brewery (in Pawcatuck). The adventure continues: appreciate the extensive heritage of Cliff Walk, take in the spiritual surroundings of Touro Synagogue, tour the old-fashioned way with a train tour, and admire all the interesting features of Ocean Drive Historic District.

To see maps, more things to do, and more tourist information, go to the Newport tour itinerary planner.

Getting from Boston to Newport by bus takes about 2 hours. Other options: drive; or do a combination of train and bus. Expect a daytime high around 80°F in July, and nighttime lows around 66°F. Wrap up your sightseeing on the 5th (Wed) early enough to drive to Sandwich.

Things to do in Newport

Historic Sites Museums Outdoors

Side Trips

Purgatory Chasm, The Glass Station, Mystic Seaport Museum, Misquamicut State Beach, Cottrell Brewery
Highlights from your plan
The Breakers ©
The Breakers
Mystic Seaport Museum ©
Mystic Seaport Museum
Ocean Drive Historic District ©
Ocean Drive Historic District

6
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Museum-lovers will appreciate Heritage Museums & Gardens and New Bedford Whaling Museum. Deepen your sense of the past at sights like Highfield Hall & Gardens and Edgartown Lighthouse. Get out of town with these interesting Sandwich side-trips: Nobska Point Lighthouse (in Woods Hole), Menemsha Public Beach (in Menemsha) and Cape Cod Maritime Museum (in Hyannis Port). Next up on the itinerary: tour the pleasant surroundings at Craigville Beach, enjoy the sand and surf at Sandy Neck Beach, grab your bike and head to Shining Sea Bikeway, and get curious at Sandwich Glass Museum.

For maps, reviews, where to stay, and other tourist information, refer to the Sandwich trip itinerary planner.

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. August in Sandwich sees daily highs of 78°F and lows of 61°F at night. Wrap up your sightseeing on the 11th (Tue) early enough to drive to Provincetown.

Things to do in Sandwich

Parks Museums Outdoors

Side Trips

Falmouth, Plymouth, Craigville Beach, John F Kennedy Hyannis Museum, Menemsha Public Beach
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation
Craigville Beach ©
Craigville Beach

6
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 get in some beach time at Race Point Beach and Herring Cove Beach. Let the collections at Pilgrim Monument & Provincetown Museum and Provincetown Art Association and Museum capture your imagination. Explore Provincetown's surroundings by going to Eastham (Coast Guard Beach, Salt Pond Visitor Center, &more) and Orleans (Addison Art Gallery & Nauset Beach). And it doesn't end there: enjoy the sand and surf at Cape Cod National Seashore, stroll through Long Point, get a new perspective on nature at Sea Space Marine Discovery Center, and take in the waterfront at MacMillan Wharf.

For maps, where to stay, and other tourist information, you can read our Provincetown day trip site .

Drive from Sandwich to Provincetown in 1.5 hours. Alternatively, you can take a bus. In August, plan for daily highs up to 78°F, and evening lows to 62°F. Wrap up your sightseeing on the 17th (Mon) to allow time to drive to Nantucket.

Things to do in Provincetown

Parks Beaches Outdoors

Side Trips

Eastham, Orleans, Corn Hill Beach, Truro Vineyards of Cape Cod, Cape Cod National Seashore
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Nauset Beach ©
Nauset Beach
Race Point Beach ©
Race Point Beach

7
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Your itinerary includes some good beach time at Jetties Beach and Madaket Beach. Get some historical perspective at Great Point Light and St Paul's Episcopal Church. There's still lots to do: see the interesting displays at Whaling Museum, tour the pleasant surroundings at Siasconset Beach, take an in-depth tour of Egan Maritime's Nantucket Shipwreck & Lifesaving Museum, and kick back and relax at Madaquecham.

For maps, photos, reviews, and tourist information, read our Nantucket journey builder app .

Traveling by car from Provincetown to Nantucket takes 3.5 hours. In August, plan for daily highs up to 76°F, and evening lows to 63°F. Finish your sightseeing early on the 24th (Mon) so you can travel to Bar Harbor.

Things to do in Nantucket

Outdoors Parks Beaches
Highlights from your plan
Jetties Beach ©
Jetties Beach
Whaling Museum ©
Whaling Museum
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse

7
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. You'll enjoy a bit of beach vacationing at Jasper Beach and Sand Beach. Let the collections at The Seal Cove Auto Museum and Cole Land Transportation Museum capture your imagination. Explore Bar Harbor's surroundings by going to Rockland Breakwater Light (in Rockland), Wreaths Across America Museum (in Columbia Falls) and Winter Harbor (Whopaints Gallery & Schoodic Point). The adventure continues: take a tour by water with Boat Tours & Water Sports, look for all kinds of wild species at Shore Path, enjoy the sand and surf at Little Hunters Beach, and stroll through Echo Lake Beach.

Plan trip to Bar Harbor with our itinerary maker to find out where to go and what to do.

Traveling by flight from Nantucket to Bar Harbor takes 5.5 hours. Alternatively, you can do a combination of flight and car; or do a combination of ferry and car. Plan for slightly colder nights when traveling from Nantucket in August since evenings lows in Bar Harbor dip to 57°F. Finish your sightseeing early on the 31st (Mon) to allow enough time to drive to Camden.

Things to do in Bar Harbor

Parks Outdoors Beaches

Side Trips

Acadia National Park, Winter Harbor, Rockland Breakwater Light, Wreaths Across America Museum, The Seal Cove Auto Museum
Highlights from your plan
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Rockland Breakwater Light ©
Rockland Breakwater Light
Jasper Beach ©
Jasper Beach

6
nights
Camden

Camden ©
Camden is a town in Knox County, Maine, United States. Your inner history buff will appreciate Pemaquid Point Lighthouse and Maine Lighthouse Museum. You'll explore and learn at Owls Head Transportation Museum and Owls Head Lighthouse. You'll find plenty of places to visit near Camden: Colby College Museum of Art (in Waterville), Coastal Maine Botanical Gardens (in Boothbay) and Marshall Point Lighthouse Museum (in Port Clyde). And it doesn't end there: learn about winemaking at Cellardoor Winery, explore the galleries of Farnsworth Art Museum, steep yourself in history at Nickels-Sortwell House, and take in the awesome beauty at Mount Battie.

To find ratings, where to stay, traveler tips, and tourist information, go to the Camden trip planner.

Drive from Bar Harbor to Camden in 2 hours. Alternatively, you can take a bus. August in Camden sees daily highs of 74°F and lows of 56°F at night. Wrap up your sightseeing on the 6th (Sun) early enough to drive to Portland.

Things to do in Camden

Museums Historic Sites Parks

Side Trips

Rockland, Owls Head, Sweetgrass Winery and Distillery, Pemaquid Point Lighthouse, Colby College Museum of Art
Highlights from your plan
Owls Head Transportation Museum ©
Owls Head Transportation Museum
Pemaquid Point Lighthouse ©
Pemaquid Point Lighthouse
Colby College Museum of Art ©
Colby College Museum of Art

8
nights
Portland

Portland ©
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.
You'll get in some beach time at Popham Beach State Park and Old Orchard Beach. Wright Museum of WWII and Portland Museum of Art will appeal to museum buffs. Change things up with these side-trips from Portland: Maine Maritime Museum (in Bath), Ogunquit (Uniques and Antiques, Marginal Way Walkway, &more) and York (George Marshall Store Gallery & Nubble Lighthouse). Next up on the itinerary: enjoy the sea views from Portland Head Light, stroll through Casco Bay, sample the tasty concoctions at Allagash Brewing Company, and get engrossed in the history at Victoria Mansion.

For traveler tips, more things to do, and other tourist information, read our Portland day trip planning website .

Drive from Camden to Portland in 2 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 73°F, and evening lows to 52°F. Finish your sightseeing early on the 14th (Mon) so you can travel back home.

Things to do in Portland

Museums Outdoors Parks

Side Trips

Ogunquit, York, Portsmouth, Portland Head Light, Old Orchard Beach
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portland Head Light ©
Portland Head Light
Nubble Lighthouse ©
Nubble Lighthouse

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