60 days in New England Itinerary

60 days in New England Itinerary

Created using Inspirock New England 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

Birthplace of American Liberty

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.
Museum-lovers will get to explore Pilgrim Monument & Provincetown Museum and Provincetown Town Hall. Visiting Herring Cove Beach and Wellfleet Bay Wildlife Sanctuary will get you outdoors. Explore the numerous day-trip ideas around Provincetown: Nauset Beach (in Orleans) and Eastham (Nauset Lighthouse, Nauset Light Beach, &more). There's lots more to do: delve into the lush surroundings at Beech Forest, Provincetown, explore the world behind art at Provincetown Art Association and Museum, get a dose of the wild on Art's Dune Tours, and enjoy the sand and surf at Marconi Beach.

To find where to stay, reviews, other places to visit, and more tourist information, you can read our Provincetown journey maker.

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 moving from Australian Western Standard Time (AWST) to Eastern Standard Time (EST) is minus 13 hours. Traveling from Perth in November, expect nights in Provincetown to be little chillier, around 39°F, while days are much colder, around 51°F. Wrap up your sightseeing on the 28th (Sun) early enough to drive to Sandwich.

Things to do in Provincetown

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Nov 24 — 28:
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Sandwich

— 5 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Do some cultural sightseeing at New Bedford Whaling Museum and Aquinnah Cliffs. You'll explore the less-touristy side of things at Gay Head Lighthouse and Seagull Beach. Get out of town with these interesting Sandwich side-trips: Nobska Point Lighthouse (in Woods Hole), Edgartown (Katama Beach/ South Beach & Edgartown Lighthouse) and Martha's Vineyard Camp meeting Association (MVCMA) (in Oak Bluffs). The adventure continues: engage your brain at Sandwich Glass Museum, contemplate the waterfront views at Cape Cod Canal, examine the collection at Heritage Museums & Gardens, and experience rural life at Coonamessett Farm.

For more things to do, where to stay, reviews, and tourist information, use the Sandwich trip maker tool.

You can drive from Provincetown to Sandwich in 1.5 hours. Another option is to take a bus. Expect a daytime high around 53°F in November, and nighttime lows around 35°F. Wrap up your sightseeing on the 3rd (Fri) to allow time to fly to Bar Harbor.

Things to do in Sandwich

Parks · Historic Sites · Museums · Outdoors

Side Trips

Find places to stay Nov 28 — Dec 3:
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Bar Harbor, Mount Desert Island

— 5 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Explore hidden gems such as Ocean Path and Precipice Trail. Escape the urban bustle at Great Head Trail and Schoodic Point. Explore the numerous day-trip ideas around Bar Harbor: Mount Hope Garden Cemetery (in Bangor) and Wonderland Trail (in Southwest Harbor). Next up on the itinerary: capture your vacation like a pro with an inspiring photography tour, explore the striking landscape at Thunder Hole, trek along Gorham Mountain Trail, and tour the pleasant surroundings at Bubble Rock.

Quickly create a custom-made itinerary for Bar Harbor using our trip planner.

Traveling by flight from Sandwich to Bar Harbor takes 3 hours. Alternatively, you can drive; or take a bus. Traveling from Sandwich in December, things will get a bit cooler in Bar Harbor: highs are around 36°F and lows about 21°F. Finish your sightseeing early on the 8th (Wed) so you can drive to Rockland.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips

Find places to stay Dec 3 — 8:
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Rockland

— 4 nights
Rockland is a city in Knox County, Maine, in the United States. Explore hidden gems such as 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). Next up on the itinerary: examine the collection at Owls Head Transportation Museum, visit High Street Historic District, enjoy the sea views from Rockland Breakwater Light, and pause for some photo ops at Andre the Seal Statue.

For where to stay, photos, more things to do, and tourist information, go to the Rockland tour itinerary planner.

Getting from Bar Harbor to Rockland by car takes about 2.5 hours. Other options: take a bus. December in Rockland sees daily highs of 37°F and lows of 22°F at night. Finish up your sightseeing early on the 12th (Sun) so you can go by car to Portland.

Things to do in Rockland

Historic Sites · Museums · Parks · Nature

Side Trips

Find places to stay Dec 8 — 12:
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Portland

— 5 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.
Maine Maritime Museum and Old Port are good opportunities to explore the local culture. Discover out-of-the-way places like Allagash Brewing Company and Strawbery Banke Museum. You'll find plenty of places to visit near Portland: Maine State Museum (in Augusta), Boothbay Region Land Trust (in Boothbay Harbor) and Maine Wildlife Park (in Gray). The adventure continues: grab your bike and head to Eastern Promenade Trail, look for all kinds of wild species at Wells Reserve at Laudholm, get engrossed in the history at USS Albacore Museum, and get to know the fascinating history of Marginal Way Walkway.

For ratings, photos, other places to visit, and other tourist information, refer to the Portland journey planner.

You can drive from Rockland to Portland in 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. December in Portland sees daily highs of 37°F and lows of 22°F at night. Finish up your sightseeing early on the 17th (Fri) so you can go by car to North Conway.

Things to do in Portland

Parks · Wildlife · Historic Sites · Museums

Side Trips

Find places to stay Dec 12 — 17:
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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.
Step out of the city life by going to Cranmore Mountain Resort and Cathedral Ledge. Do your shopping at Settlers Green and Zeb's General Store. You'll find plenty of places to visit near North Conway: Wright Museum of WWII (in Wolfeboro), Crawford Notch State Park (in Hart's Location) and Grafton Notch State Park (in Bethel). There's much more to do: look and learn at Mount Washington Observatory Weather Discovery Center, admire the majestic nature at Echo Lake State Park, admire the sheer force of Glen Ellis Falls, and glide through natural beauty at Great Glen Trails Outdoor Center.

To find more things to do, traveler tips, photos, and tourist information, read North Conway day trip tool.

You can drive from Portland to North Conway in 2 hours. Alternatively, you can do a combination of bus and taxi. Expect a daytime high around 40°F in December, and nighttime lows around 24°F. Cap off your sightseeing on the 22nd (Wed) early enough to go by car to Lincoln.

Things to do in North Conway

Parks · Nature · Winter Sports · Outdoors

Side Trips

Find places to stay Dec 17 — 22:
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Lincoln

— 4 nights
Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Let the collections at Montshire Museum of Science and Billings Farm & Museum capture your imagination. Step off the beaten path and head to The Basin at Franconia Notch State Park and Killington Resort. Change things up with these side-trips from Lincoln: Quechee (Quechee Gorge & Vermont Institute of Natural Science), Bretton Woods Canopy Tour (in Bretton Woods) and Squam Lakes Natural Science Center (in Holderness). There's lots more to do: head outdoors with Outdoor Activities, walk around Lost River Gorge and Boulder Caves, and indulge your thirst for a good beer at Harpoon Brewery.

To see traveler tips, other places to visit, and tourist information, use the Lincoln sightseeing planning app.

Traveling by car from North Conway to Lincoln takes 1.5 hours. Expect slightly colder temperatures when traveling from North Conway in December; daily highs in Lincoln reach 34°F and lows reach 19°F. Finish up your sightseeing early on the 26th (Sun) so you can travel to New Shoreham.

Things to do in Lincoln

Parks · Wildlife · Outdoors · Tours

Side Trips

Find places to stay Dec 22 — 26:
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New Shoreham, Block Island

— 2 nights
New Shoreham is a town in Washington County, Rhode Island, United States. Kick off your visit on the 27th (Mon): cast your line with a fishing tour, enjoy the sea views from South East Lighthouse, and then tour the pleasant surroundings at Mohegan Bluffs. Get ready for a full day of sightseeing on the next day: stroll through Sachem Pond Wildlife Refuge, take a leisurely stroll along Mansion Beach, and then view the masterpieces at Jessie Edwards Studio.

For where to stay, other places to visit, more things to do, and more tourist information, go to the New Shoreham online road trip planner.

Traveling by combination of flight and ferry from Lincoln to New Shoreham takes 5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus, train, and ferry. Traveling from Lincoln in December, things will get somewhat warmer in New Shoreham: highs are around 45°F and lows about 35°F. Wrap up your sightseeing on the 28th (Tue) early enough to ride a ferry to Newport.

Things to do in New Shoreham

Outdoors · Parks · Wildlife · Trails
Find places to stay Dec 26 — 28:
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Newport

— 6 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Step off the beaten path and head to Lizzie Borden House and Bellevue Avenue Historic District. Do some cultural sightseeing at Rosecliff and Thames Glass. Explore Newport's surroundings by going to Battleship Cove (in Fall River), Colt State Park (in Bristol) and Fishing Charters & Tours (in Narragansett). Spend the 30th (Thu) exploring nature at Sachuest Point National Wildlife Refuge. Next up on the itinerary: explore the world behind art at RISD Museum, enjoy the sand and surf at Sachuest Beach (Second Beach), get to know the fascinating history of Cliff Walk, and do a tasting at Newport Vineyards.

To find where to stay, more things to do, reviews, and other tourist information, read Newport vacation website.

Traveling by ferry from New Shoreham to Newport takes 2 hours. Alternatively, you can do a combination of ferry and taxi. In December in Newport, expect temperatures between 44°F during the day and 32°F at night. Wrap up your sightseeing on the 3rd (Mon) to allow time to drive to Hartford.

Things to do in Newport

Parks · Museums · Wildlife · Nature

Side Trips

Find places to stay Dec 28 — Jan 3:
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Hartford

— 6 nights
Hartford is the capital of the U.S. state of Connecticut. Discover out-of-the-way places like Wadsworth Atheneum Museum of Art and New Britain Museum of American Art. Get some historical perspective at Historic Deerfield and Gillette Castle State Park. Change things up with these side-trips from Hartford: South Deerfield (Magic Wings Butterfly Conservatory and Gardens & Yankee Candle Flagship Store), Mashantucket Pequot Museum & Research Center (in Mashantucket) and The Submarine Force Museum (in Groton). The adventure continues: get a new perspective on nature at Yale Peabody Museum of Natural History, explore the engaging exhibits at Springfield Museums, admire the majestic nature at Mount Tom State Reservation, and stroll through White Memorial Conservation Center.

To find where to stay, photos, maps, and other tourist information, read our Hartford itinerary builder tool.

Getting from Newport to Hartford by car takes about 2 hours. Other options: take a bus; or do a combination of bus and train. In January, daytime highs in Hartford are 36°F, while nighttime lows are 21°F. Cap off your sightseeing on the 9th (Sun) early enough to go by car to Lenox.

Things to do in Hartford

Museums · Parks · Nature · Wildlife

Side Trips

Find places to stay Jan 3 — 9:
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Lenox

— 5 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. The Mount, Edith Wharton's Home and National Shrine of the Divine Mercy will appeal to history buffs. You'll explore and learn at MASS MoCA and Norman Rockwell Museum. You'll find plenty of places to visit near Lenox: Vermont Country Store (in Weston), Equinox Preservation Trust (in Manchester) and Mount Greylock State Reservation (in Lanesborough). Next up on the itinerary: stroll through Pleasant Valley Sanctuary, take your sightseeing to a higher altitude at Monument Mountain, head outdoors with Outdoor Activities, and take an in-depth tour of Hancock Shaker Village.

To find where to stay, other places to visit, more things to do, and more tourist information, use the Lenox itinerary planner.

You can drive from Hartford to Lenox in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. Expect slightly colder temperatures when traveling from Hartford in January; daily highs in Lenox reach 31°F and lows reach 14°F. Finish your sightseeing early on the 14th (Fri) to allow enough time to drive to Boston.

Things to do in Lenox

Museums · Parks · Historic Sites · Wildlife

Side Trips

Find places to stay Jan 9 — 14:
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Boston

— 7 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.
Get in touch with nature at Minute Man National Historical Park and Chatham Lighthouse Beach. Sleepy Hollow Cemetery and Freedom Trail will appeal to history buffs. Explore the numerous day-trip ideas around Boston: Parker River National Wildlife Refuge (in Newburyport), Louisa May Alcott's Orchard House (in Concord) and Massabesic Audubon Center (in Auburn). There's still lots to do: admire the masterpieces at Currier Museum of Art, take in nature's colorful creations at Boston Public Garden, admire the landmark architecture of Massachusetts State House, and appreciate the history behind The Mapparium.

To see other places to visit, photos, and other tourist information, refer to the Boston travel app.

Traveling by car from Lenox to Boston takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect somewhat warmer temperatures when traveling from Lenox in January; daily highs in Boston reach 37°F and lows reach 23°F. Cap off your sightseeing on the 21st (Fri) early enough to catch the flight back home.

Things to do in Boston

Parks · Wildlife · Museums · Historic Sites

Side Trips

Find places to stay Jan 14 — 21:
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