16 days in New England Itinerary

16 days in New England Itinerary

Created using Inspirock New England trip itinerary maker

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Route & dates

16 days in New England Itinerary

Start: Cleveland
Fly:  11​h
1
Southwest Harbor, Mount Desert Island
— 1 night
Drive:  3​h 15​min
2
Rockland
— 1 night
Drive:  2​h 30​min
3
York
— 2 nights
Drive:  2​h 15​min
4
Lincoln
— 2 nights
Drive + ferry:  5​h
5
Edgartown, Martha's Vineyard
— 2 nights
Drive:  3​h
6
Nantucket
— 3 nights
Drive:  2​h 15​min
7
Provincetown
— 3 nights
Fly:  5​h 30​min
End: Cleveland

1
night
Southwest Harbor, Mount Desert Island

Southwest Harbor ©
Southwest Harbor is a town in Hancock County, Maine, United States. On the 4th (Wed), take a peaceful walk through Indian Point Blagden Preserve, then contemplate the waterfront views at Jordan Pond Path Trailhead, and then cruise along Park Loop Road. Get ready for a full day of sightseeing on the 5th (Thu): appreciate the extensive heritage of Ship Harbor Nature Trail, grab your bike and head to Carriage Roads, and then kick back and relax at Sand Beach.

For other places to visit, traveler tips, more things to do, and tourist information, go to the Southwest Harbor road trip planning tool .

Cleveland to Southwest Harbor is an approximately 11-hour flight. Plan for little chillier temperatures traveling from Cleveland in September, with highs in Southwest Harbor at 70°F and lows at 52°F. Wrap up your sightseeing on the 5th (Thu) early enough to travel to Rockland.

Things to do in Southwest Harbor

Outdoors Parks Nature

Side Trips

Acadia National Park, Indian Point Blagden Preserve, Ship Harbor Nature Trail
Highlights from your plan
Park Loop Road ©
Park Loop Road
Indian Point Blagden Preserve ©
Indian Point Blagden Preserve
Carriage Roads ©
Carriage Roads

1
night
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Start off your visit on the 6th (Fri): explore the world behind art at Farnsworth Art Museum, take your sightseeing to a higher altitude at Mount Battie, and then immerse yourself in nature at Camden Hills State Park.

To find maps, reviews, photos, and tourist information, you can read our Rockland online driving holiday planner .

Getting from Southwest Harbor to Rockland by car takes about 2.5 hours. In September, daytime highs in Rockland are 69°F, while nighttime lows are 51°F. Wrap up your sightseeing on the 6th (Fri) early enough to drive to York.

Things to do in Rockland

Nature Parks Historic Sites

Side Trip

Camden
Highlights from your plan
Mount Battie ©
Mount Battie
Farnsworth Art Museum ©
Farnsworth Art Museum
Camden Hills State Park ©
Camden Hills State Park

2
nights
York

York ©
York is a town in York County, Maine, United States, near the southern tip of the state. Kick off your visit on the 7th (Sat): kick back and relax at Ogunquit Beach, then enjoy the sea views from Cape Neddick Nubble Lighthouse, and then enjoy the sand and surf at Long Sands Beach. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Wells Beach, kick back and relax at Drakes Island Beach, and then get to know the fascinating history of Marginal Way Walkway.

To find where to stay and more tourist information, read York day trip planning website .

Traveling by car from Rockland to York takes 2.5 hours. Alternatively, you can do a combination of flight, bus, and taxi; or do a combination of bus, train, and taxi. In September, plan for daily highs up to 74°F, and evening lows to 54°F. Finish your sightseeing early on the 8th (Sun) to allow enough time to drive to Lincoln.

Things to do in York

Beaches Outdoors Parks

Side Trips

Ogunquit, Wells
Highlights from your plan
Drakes Island Beach ©
Drakes Island Beach
Marginal Way Walkway ©
Marginal Way Walkway
Ogunquit Beach ©
Ogunquit Beach

2
nights
Lincoln

Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Kick off your visit on the 9th (Mon): immerse yourself in nature at Franconia Notch State Park, take in the dramatic natural features at The Basin at Franconia Notch State Park, and then look for all kinds of wild species at Lost River Gorge and Boulder Caves. Keep things going the next day: take in the dramatic natural features at Flume Gorge, kick your exploration up a notch at some of the top local zipline courses and adventure parks, and then take in the dramatic scenery at Cascade Falls.

For maps, other places to visit, and more tourist information, read our Lincoln trip planner .

Drive from York to Lincoln in 2.5 hours. Alternatively, you can do a combination of car and bus; or do a combination of taxi and bus. Traveling from York in September, you can expect nighttime temperatures to be little chillier in Lincoln, with lows of 48°F. Cap off your sightseeing on the 10th (Tue) early enough to travel to Edgartown.

Things to do in Lincoln

Parks Nature Tours

Side Trips

Franconia, Woodstock
Highlights from your plan
Zipline
Flume Gorge ©
Flume Gorge
Franconia Notch State Park ©
Franconia Notch State Park

2
nights
Edgartown, Martha's Vineyard

Edgartown ©
Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 11th (Wed): kick back and relax at Menemsha Public Beach, then kick back and relax at Menemsha Hills, and then visit a coastal fixture at Edgartown Lighthouse. Get ready for a full day of sightseeing on the 12th (Thu): take in the dramatic natural features at Aquinnah Cliffs, then stroll through Norton Point Beach, and then enjoy the sand and surf at Katama Beach/ South Beach.

For reviews, traveler tips, photos, and other tourist information, read Edgartown trip maker tool .

You can do a combination of car and ferry from Lincoln to Edgartown in 5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and ferry. Traveling from Lincoln in September, plan for somewhat warmer nights in Edgartown, with lows around 54°F. Cap off your sightseeing on the 12th (Thu) early enough to travel to Nantucket.

Things to do in Edgartown

Parks Beaches Outdoors

Side Trips

Menemsha Hills, Menemsha Public Beach, Aquinnah Cliffs
Highlights from your plan
Menemsha Public Beach ©
Menemsha Public Beach
Menemsha Hills ©
Menemsha Hills
Aquinnah Cliffs ©
Aquinnah Cliffs

3
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. You'll get in some beach time at Madaket Beach and Cisco Beach. Get some cultural insight at Sankaty Head Lighthouse and Brant Point Lighthouse. There's much more to do: stroll through Surfside Beach, examine the collection at Whaling Museum, kick back and relax at Jetties Beach, and pause for some serene contemplation at St Paul's Episcopal Church.

To find photos, other places to visit, ratings, and other tourist information, refer to the Nantucket trip maker app .

Do a combination of bus and flight from Edgartown to Nantucket in 3 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of car and ferry. In September, plan for daily highs up to 71°F, and evening lows to 59°F. Finish your sightseeing early on the 15th (Sun) to allow enough time to travel to Provincetown.

Things to do in Nantucket

Beaches Outdoors Parks
Highlights from your plan
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse
Brant Point Lighthouse ©
Brant Point Lighthouse
Cisco Beach ©
Cisco Beach

3
nights
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.
Eschew the tourist crowds and head to Marconi Beach and Nauset Beach. Take a break from the city and head to Coast Guard Beach and Dolphin & Whale Watching. The adventure continues: kick back and relax at Herring Cove Beach, stroll through Race Point Beach, visit a coastal fixture at Highland Light, and pause for some photo ops at Pilgrim Monument & Provincetown Museum.

For reviews, maps, other places to visit, and tourist information, read Provincetown online driving holiday planner .

You can do a combination of ferry and taxi from Nantucket to Provincetown in 2.5 hours. Other options are to do a combination of ferry and bus; or fly. In September in Provincetown, expect temperatures between 71°F during the day and 57°F at night. Finish your sightseeing early on the 18th (Wed) to allow enough time to travel back home.

Things to do in Provincetown

Outdoors Beaches Parks

Side Trips

Wellfleet, Nauset Beach, Coast Guard Beach, Highland Light
Highlights from your plan
Dolphin & Whale Watching
Highland Light ©
Highland Light
Race Point Beach ©
Race Point Beach

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