60 days in New England Itinerary

60 days in New England Itinerary

Created using Inspirock New England trip planner
Make it your trip
Fly to Logan International Airport, Drive to Provincetown
1
Provincetown
— 4 nights
Drive
2
Sandwich
— 5 nights
Fly
3
Bar Harbor, Mount Desert Island
— 5 nights
Drive
4
Rockland
— 4 nights
Drive
5
Portland
— 5 nights
Drive
6
North Conway
— 5 nights
Drive
7
Lincoln
— 4 nights
Fly to Boston, Ferry to New Shoreham
8
New Shoreham, Block Island
— 2 nights
Ferry
9
Newport
— 6 nights
Drive
10
Hartford
— 6 nights
Drive
11
Lenox
— 5 nights
Drive
12
Boston
— 7 nights
Fly

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Provincetown — 4 nights

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 explore the less-touristy side of things at Herring Cove Beach and Cape Cod National Seashore. You'll explore and learn at Pilgrim Monument & Provincetown Museum and Provincetown Art Association and Museum. You'll find plenty of places to visit near Provincetown: Nauset Beach (in Orleans) and Eastham (Nauset Lighthouse, Nauset Light Beach, &more). And it doesn't end there: stroll through Beech Forest, Provincetown, ponder the world of politics at Provincetown Town Hall, get a dose of the wild on Art's Dune Tours, and enjoy the sand and surf at Marconi Beach.

To find ratings, maps, traveler tips, and other tourist information, read Provincetown travel itinerary planner.

Perth, Australia to Provincetown is an approximately 34.5-hour combination of flight and car. You can also do a combination of flight and ferry. The time zone difference when traveling from Perth to Provincetown is minus 13 hours. While traveling from Perth, expect cooler days and little chillier nights in Provincetown, ranging from highs of 12°C to lows of 4°C. Wrap up your sightseeing on the 9th (Tue) early enough to drive to Sandwich.
Parks · Outdoors · Beaches · Nature
Side Trips

Sandwich — 5 nights

Sandwich is a town in Barnstable County, Massachusetts, United States. Visit Gay Head Lighthouse and Edgartown Lighthouse for their historical value. Get in touch with nature at Aquinnah Cliffs and Seagull Beach. Get out of town with these interesting Sandwich side-trips: New Bedford Whaling Museum (in New Bedford), Katama Beach/ South Beach (in Edgartown) and Nobska Point Lighthouse (in Woods Hole). There's much more to do: get curious at Sandwich Glass Museum, examine the collection at Heritage Museums & Gardens, stop by Martha's Vineyard Camp meeting Association (MVCMA), and get up close to creatures of the deep with Hyannis Whale Watcher Cruises.

To see ratings, photos, maps, and more tourist information, you can read our Sandwich online day trip planner.

Getting from Provincetown to Sandwich by car takes about 1.5 hours. Other options: take a bus. November in Sandwich sees daily highs of 13°C and lows of 1°C at night. Cap off your sightseeing on the 14th (Sun) early enough to catch the flight to Bar Harbor.
Parks · Historic Sites · Museums · Outdoors
Side Trips

Bar Harbor, Mount Desert Island — 5 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Eschew the tourist crowds and head to Ocean Path and Great Head Trail. Get outdoors at Photography Tours and Champlain Mountain & Beehive Loop Trail. Change things up with these side-trips from Bar Harbor: Wonderland Trail (in Southwest Harbor), Schoodic Point (in Winter Harbor) and Mount Hope Garden Cemetery (in Bangor). There's still lots to do: trek along Precipice Trail, enjoy the sand and surf at Sand Beach, explore the activities along Jordan Pond Path Trailhead, and relax and rejuvenate at some of the best spas.

For traveler tips, photos, ratings, and more tourist information, read Bar Harbor vacation tool.

Traveling by flight from Sandwich to Bar Harbor takes 3 hours. Alternatively, you can drive; or take a bus. Prepare for little chillier weather when traveling from Sandwich in November: high temperatures in Bar Harbor hover around 9°C and lows are around -1°C. Wrap up your sightseeing on the 19th (Fri) to allow time to drive to Rockland.
Parks · Outdoors · Trails · Nature
Side Trips

Rockland — 4 nights

Rockland is a city in Knox County, Maine, in the United States. Museum-lovers will get to explore Farnsworth Art Museum and Marshall Point Lighthouse Museum. Escape the urban bustle at Mount Battie and Camden Hills State Park. Get out of town with these interesting Rockland side-trips: Pemaquid Point Lighthouse (in Bristol) and Colby College Museum of Art (in Waterville). There's much more to do: examine the collection at Owls Head Transportation Museum, do a tasting at Cellardoor Winery, look for gifts at Maine State Prison Store, and pause for some photo ops at Andre the Seal Statue.

To find photos, traveler tips, reviews, and more tourist information, you can read our Rockland online travel planner.

You can drive from Bar Harbor to Rockland in 2.5 hours. Other options are to drive; or take a bus. In November, plan for daily highs up to 9°C, and evening lows to -1°C. Finish your sightseeing early on the 23rd (Tue) so you can drive to Portland.
Historic Sites · Museums · Parks · Nature
Side Trips

Portland — 5 nights

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.
Maine Maritime Museum and Strawbery Banke Museum are good opportunities to explore the local culture. You'll discover tucked-away gems like Allagash Brewing Company and USS Albacore Museum. Venture out of the city with trips to Maine Wildlife Park (in Gray), Boothbay Region Land Trust (in Boothbay Harbor) and Maine State Museum (in Augusta). There's still lots to do: trek along Eastern Promenade Trail, tour the pleasant surroundings at Rachel Carson National Wildlife Refuge, enjoy the sand and surf at Wells Beach, and wander the streets of Old Port.

To find reviews, ratings, and tourist information, go to the Portland trip itinerary planning tool.

You can drive from Rockland to Portland in 2 hours. Other options are to take a bus; or do a combination of bus and train. In November, daytime highs in Portland are 11°C, while nighttime lows are -1°C. Finish up your sightseeing early on the 28th (Sun) so you can go by car to North Conway.
Parks · Historic Sites · Wildlife · Museums
Side Trips

North Conway — 5 nights

North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Explore hidden gems such as Cranmore Mountain Resort and Cathedral Ledge. For shopping fun, head to Settlers Green or Zeb's General Store. Change things up with these side-trips from North Conway: Wright Museum of WWII (in Wolfeboro), Grafton Notch State Park (in Bethel) and Crawford Notch State Park (in Hart's Location). There's lots more to do: see the sky in a new way at Mount Washington Observatory Weather Discovery Center, take a peaceful walk through White Mountain National Forest, take in the architecture and atmosphere at The Little White Church, and stroll through Great Glen Trails Outdoor Center.

To see photos, more things to do, traveler tips, and tourist information, read our North Conway road trip app.

Traveling by car from Portland to North Conway takes 2 hours. Alternatively, you can do a combination of bus and taxi. November in North Conway sees daily highs of 11°C and lows of 0°C at night. Wrap up your sightseeing on the 3rd (Fri) early enough to drive to Lincoln.
Parks · Nature · Winter Sports · Outdoors
Side Trips

Lincoln — 4 nights

Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Get outdoors at The Basin at Franconia Notch State Park and Montshire Museum of Science. You'll explore the less-touristy side of things at Off-Road Tours and Quechee Gorge. Explore Lincoln's surroundings by going to Vermont Institute of Natural Science (VINS) (in Quechee), Squam Lakes Natural Science Center (in Holderness) and Bretton Woods Canopy Tour (in Bretton Woods). There's much more to do: get engrossed in the history at Billings Farm & Museum, walk around Lost River Gorge and Boulder Caves, fly down the slopes at Killington Resort, and sample the tasty concoctions at Harpoon Brewery.

To find ratings, traveler tips, and tourist information, refer to the Lincoln trip itinerary planner.

Traveling by car from North Conway to Lincoln takes 1.5 hours. Expect little chillier temperatures when traveling from North Conway in December; daily highs in Lincoln reach 1°C and lows reach -8°C. Finish up your sightseeing early on the 7th (Tue) so you can travel to New Shoreham.
Parks · Wildlife · Outdoors · Tours
Side Trips

New Shoreham, Block Island — 2 nights

New Shoreham is a town in Washington County, Rhode Island, United States. Kick off your visit on the 8th (Wed): see what you can catch with a fishing tour, visit a coastal fixture at South East Lighthouse, and then explore the striking landscape at Mohegan Bluffs. On the 9th (Thu), you'll have a packed day of sightseeing: stroll through Sachem Pond Wildlife Refuge, then take in the waterfront at Mansion Beach, and then view the masterpieces at Jessie Edwards Studio.

For ratings, maps, reviews, and other tourist information, read our New Shoreham trip maker site.

You can do a combination of flight and ferry from Lincoln to New Shoreham in 5 hours. Other options are to do a combination of bus and ferry; or do a combination of bus, train, and ferry. Prepare for somewhat warmer weather when traveling from Lincoln in December: high temperatures in New Shoreham hover around 8°C and lows are around 1°C. Finish your sightseeing early on the 9th (Thu) so you can ride a ferry to Newport.
Outdoors · Parks · Wildlife · Beaches

Newport — 6 nights

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Take a break from the city and head to Bellevue Avenue Historic District and Fishing Charters & Tours. Discover out-of-the-way places like Lizzie Borden House and Newport Car Museum. Get out of town with these interesting Newport side-trips: Battleship Cove (in Fall River), Colt State Park (in Bristol) and RISD Museum (in Providence). Spend the 11th (Sat) exploring nature at Sachuest Point National Wildlife Refuge. The adventure continues: see the interesting displays at Rosecliff, wander the streets of Thames Street, get to know the fascinating history of Cliff Walk, and walk around Fort Adams State Park.

For ratings, maps, where to stay, and other tourist information, go to the Newport trip website.

Traveling by ferry from New Shoreham to Newport takes 2 hours. Alternatively, you can do a combination of ferry and taxi. In December, plan for daily highs up to 7°C, and evening lows to 0°C. Finish your sightseeing early on the 15th (Wed) so you can drive to Hartford.
Parks · Museums · Wildlife · Nature
Side Trips

Hartford — 6 nights

Hartford is the capital of the U.S. state of Connecticut. Step out of the city life by going to Kent Falls State Park and Magic Wings Butterfly Conservatory and Gardens. Satisfy your inner culture vulture at Wadsworth Atheneum Museum of Art and New Britain Museum of American Art. Venture out of the city with trips to Historic Deerfield (in Deerfield), Mashantucket Pequot Museum & Research Center (in Mashantucket) and Yankee Candle Flagship Store (in South Deerfield). There's much more to do: get a new perspective on nature at Yale Peabody Museum of Natural History, explore the world behind art at Yale University Art Gallery, see the interesting displays at The Submarine Force Museum, and immerse yourself in nature at Silver Sands State Park.

To see more things to do, other places to visit, maps, and more tourist information, use the Hartford holiday builder.

You can drive from Newport to Hartford in 2 hours. Other options are to take a bus; or do a combination of bus and train. In December, plan for daily highs up to 6°C, and evening lows to -2°C. Finish your sightseeing early on the 21st (Tue) to allow enough time to drive to Lenox.
Museums · Parks · Nature · Wildlife
Side Trips

Lenox — 5 nights

Lenox is an affluent town in Berkshire County, Massachusetts, United States. Visiting Pleasant Valley Sanctuary and Zipline will get you outdoors. Let the collections at The Mount, Edith Wharton's Home and Hancock Shaker Village capture your imagination. Change things up with these side-trips from Lenox: Equinox Preservation Trust (in Manchester), Mount Greylock State Reservation (in Lanesborough) and Vermont Country Store (in Weston). And it doesn't end there: admire the masterpieces at MASS MoCA, contemplate in the serene atmosphere at National Shrine of the Divine Mercy, take in the awesome beauty at Monument Mountain, and take an in-depth tour of Bennington Museum.

For reviews, traveler tips, more things to do, and other tourist information, use the Lenox trip maker tool.

Drive from Hartford to Lenox in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Prepare for slightly colder weather when traveling from Hartford in December: high temperatures in Lenox hover around 3°C and lows are around -5°C. Wrap up your sightseeing on the 26th (Sun) early enough to drive to Boston.
Museums · Parks · Wildlife · Historic Sites
Side Trips

Boston — 7 nights

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.
You'll discover tucked-away gems like Minute Man National Historical Park and The Mapparium. Museum of Fine Arts and Freedom Trail are good opportunities to explore the local culture. Venture out of the city with trips to Concord (Louisa May Alcott's Orchard House & Sleepy Hollow Cemetery), Massabesic Audubon Center (in Auburn) and Parker River National Wildlife Refuge (in Newburyport). There's lots more to do: admire the masterpieces at Currier Museum of Art, walk around Boston Public Garden, admire the striking features of Massachusetts State House, and get engrossed in the history at Boston Tea Party Ships & Museum.

To see reviews, more things to do, traveler tips, and tourist information, refer to the Boston online trip itinerary planner.

Getting from Lenox to Boston by car takes about 2.5 hours. Other options: take a bus; or do a combination of bus and train. Plan for a bit warmer temperatures traveling from Lenox in December, with highs in Boston at 7°C and lows at 0°C. Wrap up your sightseeing on the 2nd (Sun) to allow time to fly back home.
Parks · Wildlife · Museums · Nature
Side Trips