44 days in Massachusetts, Maine & New Hampshire Itinerary

44 days in Massachusetts, Maine & New Hampshire Itinerary

Created using Inspirock United States travel route planner

Make it your trip
Fly
1
Nantucket
— 3 nights
Ferry to Harwich Port, Harwich, MA, Taxi to Chatham
2
Chatham
— 2 nights
Drive
3
Provincetown
— 4 nights
Drive
4
Sandwich
— 2 nights
Drive
5
Boston
— 6 nights
Drive
6
Kennebunkport
— 2 nights
Drive
7
Ogunquit
— 3 nights
Drive
8
North Conway
— 4 nights
Drive
9
Portland
— 4 nights
Drive
10
South Deerfield
— 2 nights
Drive
11
Rockland
— 3 nights
Drive
12
Acadia National Park, Mount Desert Island
— 2 nights
Drive
13
Bar Harbor, Mount Desert Island
— 4 nights
Fly

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Nantucket

— 3 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Get some historical perspective at Milestone Bog and Greater Light. Explore hidden gems such as Altar Rock and Windswept Bog. There's much more to do: pause for some serene contemplation at Nantucket United Methodist Church, steep yourself in history at Old Gaol, examine the collection at Nantucket Lightship Basket Museum, and look for all kinds of wild species at Coskata-Coatue Wildlife Refuge.

For other places to visit, traveler tips, where to stay, and other tourist information, read Nantucket online trip planner.

London, UK to Nantucket is an approximately 11.5-hour flight. The time zone difference when traveling from London to Nantucket is minus 5 hours. In April, daytime highs in Nantucket are 13°C, while nighttime lows are 4°C. Wrap up your sightseeing on the 4th (Sat) to allow time to travel to Chatham.

Things to do in Nantucket

Historic Sites · Parks · Wildlife · Beaches

Chatham

— 2 nights
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. On the 5th (Sun), tour the pleasant surroundings at Harding Beach, browse for treasures at Maps of Antiquity, and then see what you can catch with a fishing tour. On the 6th (Mon), you'll have a packed day of sightseeing: stroll the grounds of Cove Burying Ground, get engrossed in the history at Stony Brook Grist Mill and Museum, then enjoy the sand and surf at Ridgevale Beach, and finally steep yourself in history at Chatham's Godfrey Windmill.

For reviews, ratings, other places to visit, and other tourist information, go to the Chatham trip maker website.

You can do a combination of ferry and taxi from Nantucket to Chatham in 2.5 hours. Another option is to do a combination of ferry and bus. In April, plan for daily highs up to 13°C, and evening lows to 4°C. Cap off your sightseeing on the 6th (Mon) early enough to go by car to Provincetown.

Things to do in Chatham

Outdoors · Beaches · Parks · Wildlife

Side Trips

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.
Pilgrim Monument & Provincetown Museum and Provincetown Town Hall will appeal to museum buffs. Discover out-of-the-way places like Wellfleet Bay Wildlife Sanctuary and Cape Cod Provincelands Trail. The adventure continues: kick back and relax at Race Point Beach, view the masterpieces at Cortile Gallery, tour the pleasant surroundings at Corn Hill Beach, and see the interesting displays at Provincetown Art Association and Museum.

To find photos, other places to visit, more things to do, and other tourist information, go to the Provincetown visit app.

Drive from Chatham to Provincetown in an hour. Alternatively, you can take a bus. April in Provincetown sees daily highs of 12°C and lows of 4°C at night. Wrap up your sightseeing on the 10th (Fri) early enough to drive to Sandwich.

Things to do in Provincetown

Parks · Outdoors · Beaches · Museums

Side Trips

Sandwich

— 2 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Start off your visit on the 11th (Sat): tour the pleasant surroundings at Green Briar Nature Center and Jam Kitchen, then examine the collection at Heritage Museums & Gardens, then explore the world behind art at Sandwich Glass Museum, and finally admire the majestic nature at National Monument to the Forefathers. Keep things going the next day: contemplate the long history of Lizzie Borden House, see the interesting displays at New Bedford Whaling Museum, then view the masterpieces at McDermott Glass Studio, and finally look for all kinds of wild species at Sandwich Fish Hatchery.

To find traveler tips, other places to visit, maps, and other tourist information, use the Sandwich driving holiday planning site.

You can drive from Provincetown to Sandwich in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 14°C in April, and nighttime lows around 2°C. Wrap up your sightseeing on the 12th (Sun) early enough to drive to Boston.

Things to do in Sandwich

Museums · Parks · Wildlife · Historic Sites

Side Trips

Boston

— 6 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.
Popular historic sites such as Trinity Church and HarborWalk are in your itinerary. Escape the urban bustle at Crane Beach and Purgatory Chasm State Reservation. Change things up with these side-trips from Boston: Worcester Art Museum (in Worcester), Minute Man National Historical Park (in Concord) and Museum of Russian Icons (in Clinton). Next up on the itinerary: see where the action happens at TD Garden, wander the streets of Back Bay, steep yourself in history at Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, and stop by North End.

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

You can drive from Sandwich to Boston in 1.5 hours. Alternatively, you can take a bus. In April, plan for daily highs up to 15°C, and evening lows to 5°C. Finish your sightseeing early on the 18th (Sat) to allow enough time to drive to Kennebunkport.

Things to do in Boston

Parks · Historic Sites · Shopping · Museums

Side Trips

Kennebunkport

— 2 nights
Kennebunkport is a town in York County, Maine, United States. Start off your visit on the 19th (Sun): look for all kinds of wild species at East Point Sanctuary, then visit a coastal fixture at Wood Island Lighthouse, and then kick back and relax at Mother's Beach. On the 20th (Mon), you'll have a packed day of sightseeing: take in the exciting artwork at Mast Cove Gallery, view the masterpieces at W. Robert Paine Gallery, then look for gifts at Maine-ly Drizzle, and finally shop like a local with Compliments.

To find traveler tips, reviews, more things to do, and tourist information, refer to the Kennebunkport trip itinerary site.

Getting from Boston to Kennebunkport by car takes about 2 hours. Other options: take a bus; or do a combination of train and bus. Traveling from Boston in April, you can expect nighttime temperatures to be little chillier in Kennebunkport, with lows of -1°C. Cap off your sightseeing on the 20th (Mon) early enough to go by car to Ogunquit.

Things to do in Kennebunkport

Shopping · Museums · Parks · Historic Sites

Side Trips

Ogunquit

— 3 nights
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Get some cultural insight at Marginal Way Walkway and Ogunquit Heritage Museum. Visit Ogunquit Beach and Drakes Island Beach for some beach relaxation. You'll find plenty of places to visit near Ogunquit: Emery Farm (in Durham), Stoneface Brewing (in Newington) and Woodman Institute Museum (in Dover). There's lots more to do: stop by Spoiled Rotten, get lost in a book at Ogunquit Memorial Library, browse for treasures at Uniques and Antiques, and get outside with Fisherman's Walk.

To see maps, more things to do, other places to visit, and more tourist information, you can read our Ogunquit trip planning website.

Ogunquit is just a short distance from Kennebunkport. Expect a daytime high around 14°C in April, and nighttime lows around -1°C. Wrap up your sightseeing on the 23rd (Thu) to allow time to drive to North Conway.

Things to do in Ogunquit

Parks · Outdoors · Beaches · Museums

Side Trips

North Conway

— 4 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.
You'll explore and learn at MWV Children's Museum and St. Johnsbury Athenaeum. Step off the beaten path and head to Cranmore Mountain Resort and Mount Washington Observatory Weather Discovery Center. When in North Conway, make a side trip to see Franconia Notch in Franconia, approximately Franconia away. Next up on the itinerary: explore the striking landscape at Cathedral Ledge, take in the architecture and atmosphere at The Little White Church, identify plant and animal life at Dahl Wildlife Sanctuary, and learn about winemaking at White Mountain Winery.

To find ratings, other places to visit, where to stay, and tourist information, read our North Conway trip maker tool.

Traveling by car from Ogunquit to North Conway takes 2 hours. Alternatively, you can take a bus. Traveling from Ogunquit in April, you can expect nighttime temperatures to be somewhat warmer in North Conway, with lows of 2°C. Finish your sightseeing early on the 27th (Mon) to allow enough time to drive to Portland.

Things to do in North Conway

Parks · Outdoors · Museums · Nature

Side Trips

Portland

— 4 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.
Appreciate the collections at 5th Maine Museum and Tate House Museum. Take a break from the city and head to Back Cove Trail and Reid State Park. There's much more to do: grab your bike and head to Eastern Promenade Trail, brush up on your knowledge of spirits at Maine Craft Distilling, stop by Edgecomb Potters, and contemplate the long history of Fort Gorges.

To find photos, more things to do, ratings, and tourist information, go to the Portland tour builder.

Traveling by car from North Conway to Portland takes 2 hours. Alternatively, you can do a combination of taxi and bus. In April in Portland, expect temperatures between 13°C during the day and 1°C at night. Finish your sightseeing early on the 1st (Fri) to allow enough time to travel to South Deerfield.

Things to do in Portland

Parks · Outdoors · Museums · Historic Sites

Side Trip

South Deerfield

— 2 nights
South Deerfield is a census-designated place (CDP) in Deerfield, Franklin County, Massachusetts, United States. Eschew the tourist crowds and head to Yankee Candle Flagship Store and Black Birch Vineyard. Frary House and Shelburne Falls Trolley Museum are good opportunities to explore the local culture. Change things up with a short trip to Bearsden Conservation Area in Athol (about 54 minutes away). The adventure continues: get engrossed in the history at Memorial Hall Museum, don't miss a visit to The New England Peace Pagoda, relax in the rural setting at Clarkdale Fruit Farms, and look for all kinds of wild species at Bullitt Reservation.

For traveler tips, more things to do, where to stay, and other tourist information, use the South Deerfield trip builder app.

You can drive from Portland to South Deerfield in 3.5 hours. While traveling from Portland, expect a bit warmer days and about the same nights in South Deerfield, ranging from highs of 24°C to lows of 8°C. Wrap up your sightseeing on the 4th (Mon) to allow time to travel to Rockland.

Things to do in South Deerfield

Museums · Parks · Wildlife · Shopping

Side Trips

Rockland

— 3 nights
Rockland is a city in Knox County, Maine, in the United States. Your inner history buff will appreciate Maine Lighthouse Museum and Castle Tucker. Your cultural itinerary includes sights like Colby College Museum of Art and Coastal Children's Museum. Go for a jaunt from Rockland to Union to see Sweetgrass Farm Winery and Distillery about 42 minutes away. There's lots more to do: admire the masterpieces at Center for Maine Contemporary Art (CMCA), get a taste of the local shopping with Linda Bean’s Maine Wyeth Gallery, see the interesting displays at Sail Power and Steam Museum, and stop by Fiore Artisan Olive Oils and Vinegars.

Before you visit Rockland, use our trip planner to discover what you can do and see there.

Getting from South Deerfield to Rockland by car takes about 4.5 hours. Other options: do a combination of car and flight. Expect a bit cooler weather when traveling from South Deerfield in May: highs in Rockland hover around 17°C, while lows dip to 7°C. Finish your sightseeing early on the 7th (Thu) to allow enough time to drive to Acadia National Park.

Things to do in Rockland

Museums · Historic Sites · Parks · Outdoors

Side Trips

Acadia National Park, Mount Desert Island

— 2 nights

First Eastern National Park

The first national park east of the Mississippi River, Acadia National Park draws visitors with its rugged landscape of ocean shoreline, low-slung granite mountains, dense woodlands, and pristine lakes.
On the 8th (Fri), trek along Beech Mountain Trail, tour the pleasant surroundings at Little Hunters Beach, and then witness a stunning natural landmark at Sieur de Monts Spring. Here are some ideas for day two: take your sightseeing to a higher altitude at Pemetic Mountain, get engrossed in the history at Somesville Historical Museum and Gardens, and then tour the pleasant surroundings at Heart of Acadia Loop.

For where to stay and other tourist information, you can read our Acadia National Park trip maker website.

You can drive from Rockland to Acadia National Park in 2.5 hours. Another option is to take a bus. In May, plan for daily highs up to 18°C, and evening lows to 7°C. Wrap up your sightseeing on the 9th (Sat) to allow time to drive to Bar Harbor.

Things to do in Acadia National Park

Parks · Nature · Outdoors · Trails

Side Trip

Bar Harbor, Mount Desert Island

— 4 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Take a break from the city and head to Bangor City Forest and Jasper Beach. Give yourself a bit of retail therapy at Little Village Gifts and A Little Mad. You'll find plenty of places to visit near Bar Harbor: Woodlawn Museum (in Ellsworth), Catherine Hill Winery (in Cherryfield) and Orono Bog Boardwalk (in Orono). There's still lots to do: relax and rejuvenate at some of the best spas, pause for some serene contemplation at St. Saviour's Church :, go for a walk through Compass Harbor Trail, and do a tasting at Bartlett Maine Estate Winery.

To find reviews, photos, maps, and other tourist information, you can read our Bar Harbor road trip planner.

Bar Harbor is very close to Acadia National Park. Expect a daytime high around 18°C in May, and nighttime lows around 7°C. Cap off your sightseeing on the 13th (Wed) early enough to travel back home.

Things to do in Bar Harbor

Parks · Outdoors · Museums · Shopping

Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.

Maine travel guide

4.6
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.

New Hampshire travel guide

4.6
Scenic Drive · Geologic Formations · Ski Areas
The Granite State
One of the country's smallest and least populous states, New Hampshire's wealth of recreational offerings make it a popular vacation destination. Its many pristine natural areas attract skiers, snowmobilers, hikers, and mountaineers from around the world. Named after a county in England, New Hampshire was the first of the North American colonies to establish a government independent of Great Britain's authority. Though New Hampshire's official nickname refers to its extensive granite formations and quarries, the state's license plates carry the motto "Live Free or Die," reflecting the sense of independence prized by the famously terse natives. Find out why America's artists continue to find inspiration in New Hampshire by taking a trip to its quaint villages and sightseeing in the area's old colonial towns.