44 days in Massachusetts, Maine & New Hampshire Itinerary

44 days in Massachusetts, Maine & New Hampshire Itinerary

Created using Inspirock United States travel route planner

Plan created by another user. Make it yours

Route & dates

1
Nantucket
— 3 nights
2
Chatham
— 2 nights
3
Provincetown
— 4 nights
4
Sandwich
— 2 nights
5
Boston
— 6 nights
6
Kennebunkport
— 2 nights
7
Ogunquit
— 3 nights
8
North Conway
— 4 nights
9
Portland
— 4 nights
10
South Deerfield
— 2 nights
11
Rockland
— 3 nights
12
Acadia National Park, Mount Desert Island
— 2 nights
13
Bar Harbor, Mount Desert Island
— 4 nights

3
nights
Nantucket

Nantucket ©
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 Nantucket United Methodist Church. There's still lots to do: look for all kinds of wild species at Coskata-Coatue Wildlife Refuge, contemplate the long history of Old Gaol, see the interesting displays at Nantucket Lightship Basket Museum, and make a trip to St Paul's Episcopal Church.

Start your trip to Nantucket by creating a personalized itinerary on Inspirock.

London, UK to Nantucket is an approximately 11.5-hour flight. You'll gain 5 hours traveling from London to Nantucket due to the time zone difference. April in Nantucket sees daily highs of 13°C and lows of 4°C at night. Finish your sightseeing early on the 4th (Sat) to allow enough time to travel to Chatham.

Things to do in Nantucket

Historic Sites · Parks · Wildlife
Highlights from your plan
Greater Light ©
Greater Light
Nobadeer ©
Nobadeer
Coskata-Coatue Wildlife Refuge ©
Coskata-Coatue Wildlife Refuge

2
nights
Chatham

Chatham ©
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 · Parks · Beaches

Side Trips

Cove Burying Ground, Stony Brook Grist Mill and Museum
Highlights from your plan
Maps of Antiquity ©
Maps of Antiquity
Harding Beach ©
Harding Beach
Cove Burying Ground ©
Cove Burying Ground

4
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.
Pilgrim Monument & Provincetown Museum and Sea Space Marine Discovery Center will appeal to museum buffs. Discover out-of-the-way places like Wellfleet Bay Wildlife Sanctuary and Provincetown Town Hall. The adventure continues: kick back and relax at Race Point Beach, view the masterpieces at Cortile Gallery, explore the landscape on two wheels at Province Lands Bike Trail, and admire the masterpieces 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

Side Trips

Wellfleet Bay Wildlife Sanctuary, Corn Hill Beach, Atlantic Spice Company
Highlights from your plan
Long Point ©
Long Point
Wellfleet Bay Wildlife Sanctuary ©
Wellfleet Bay Wildlife Sanctuary
Cape Cod Provincelands Trail ©
Cape Cod Provincelands Trail

2
nights
Sandwich

Sandwich
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

Side Trips

New Bedford Whaling Museum, Lizzie Borden House, National Monument to the Forefathers
Highlights from your plan
Lizzie Borden House
Lizzie Borden House
New Bedford Whaling Museum ©
New Bedford Whaling Museum
Heritage Museums & Gardens ©
Heritage Museums & Gardens

6
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.
Popular historic sites such as Trinity Church and Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill are in your itinerary. Escape the urban bustle at Crane Beach and Castle Island. Change things up with these side-trips from Boston: Purgatory Chasm State Reservation (in Sutton), Minute Man National Historical Park (in Concord) and Worcester Art Museum (in Worcester). Next up on the itinerary: catch a live event at TD Garden, see the interesting displays at Museum of Russian Icons, pause for some photo ops at The Mapparium, and stop by North End.

To see maps, reviews, ratings, and other tourist information, read our Boston trip itinerary maker website.

Traveling by car from Sandwich to Boston takes 1.5 hours. Alternatively, you can take a bus. In April, daytime highs in Boston are 15°C, while nighttime lows are 5°C. Cap off your sightseeing on the 18th (Sat) early enough to go by car to Kennebunkport.

Things to do in Boston

Parks · Historic Sites · Shopping

Side Trips

Purgatory Chasm State Reservation, Minute Man National Historical Park, Worcester Art Museum, Buckman Tavern, Crane Beach
Highlights from your plan
Crane Beach ©
Crane Beach
Minute Man National Historical Park ©
Minute Man National Historical Park
Museum of Russian Icons ©
Museum of Russian Icons

2
nights
Kennebunkport

Kennebunkport ©
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

Side Trips

Biddeford Pool, Mother's Beach
Highlights from your plan
Maine-ly Drizzle ©
Maine-ly Drizzle
Wood Island Lighthouse ©
Wood Island Lighthouse
East Point Sanctuary ©
East Point Sanctuary

3
nights
Ogunquit

Ogunquit ©
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: Woodman Institute Museum (in Dover), Stoneface Brewing (in Newington) and Emery Farm (in Durham). 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

Side Trips

Woodman Institute Museum, Stoneface Brewing, Emery Farm, Fisherman's Walk, Portsmouth Harbor Lighthouse
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Drakes Island Beach ©
Drakes Island Beach
Ogunquit Beach ©
Ogunquit Beach

4
nights
North Conway

North Conway ©
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

Side Trips

The Little White Church, St. Johnsbury Athenaeum, Franconia Notch
Highlights from your plan
Cranmore Mountain Resort ©
Cranmore Mountain Resort
Cathedral Ledge ©
Cathedral Ledge

4
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.
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 still lots to do: brush up on your knowledge of spirits at Maine Craft Distilling, explore the different monuments and memorials at Eastern Cemetery, steep yourself in history at Fort Gorges, and examine the collection at Maine Jewish Museum.

To find where to stay, reviews, ratings, and more tourist information, you can read our Portland trip planner.

You can drive from North Conway to Portland in 2 hours. Alternatively, you can do a combination of taxi and bus. April in Portland sees daily highs of 13°C and lows of 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

Museums · Historic Sites · Parks

Side Trip

Reid State Park
Highlights from your plan
Maine Jewish Museum ©
Maine Jewish Museum
5th Maine Museum ©
5th Maine Museum
Cellardoor at The Point ©
Cellardoor at The Point

2
nights
South Deerfield

South Deerfield ©
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: identify plant and animal life at Bullitt Reservation, don't miss a visit to The New England Peace Pagoda, relax in the rural setting at Clarkdale Fruit Farms, and take an in-depth tour of Memorial Hall Museum.

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 · Wildlife · Parks

Side Trips

Deerfield, Bullitt Reservation, Black Birch Vineyard, Bearsden Conservation Area, Shelburne Falls Trolley Museum
Highlights from your plan
Yankee Candle Flagship Store ©
Yankee Candle Flagship Store
Frary House ©
Frary House
Memorial Hall Museum ©
Memorial Hall Museum

3
nights
Rockland

Rockland ©
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 Olson House. 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

Side Trips

Camden, Sweetgrass Farm Winery and Distillery, Colby College Museum of Art, Castle Tucker, Linda Bean’s Maine Wyeth Gallery
Highlights from your plan
Colby College Museum of Art ©
Colby College Museum of Art
Maine Lighthouse Museum ©
Maine Lighthouse Museum
Olson House ©
Olson House

2
nights
Acadia National Park, Mount Desert Island

Acadia 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

Side Trip

Somesville Historical Museum and Gardens
Highlights from your plan
Little Hunters Beach ©
Little Hunters Beach
Heart of Acadia Loop ©
Heart of Acadia Loop
Sieur de Monts Spring ©
Sieur de Monts Spring

4
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
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), Orono Bog Boardwalk (in Orono) and Catherine Hill Winery (in Cherryfield). There's still lots to do: relax and rejuvenate at some of the best spas, get a new perspective on nature at George B. Dorr Museum of Natural History, take in the spiritual surroundings of St. Saviour's Church :, and learn about winemaking at Bartlett Maine Estate Winery.

For photos, reviews, where to stay, and more tourist information, read Bar Harbor holiday planning tool.

Bar Harbor is very close to Acadia National Park. In May, plan for daily highs up to 18°C, and evening lows to 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

Side Trips

Woodlawn Museum, Bartlett Maine Estate Winery, Orono Bog Boardwalk, Jasper Beach, Catherine Hill Winery
Highlights from your plan
Bangor City Forest ©
Bangor City Forest
St. Saviour's Church : ©
St. Saviour's Church :
Spas

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