16 days in New England Itinerary

16 days in New England Itinerary

Created using Inspirock New England planner

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Route & dates

16 days in New England Itinerary

Start: Washington DC
Fly:  3​h
1
Boston
— 3 nights
Drive:  1​h 30​min
2
Ogunquit
— 2 nights
Drive:  2​h
3
North Conway
— 3 nights
Drive:  5​h 15​min
4
Provincetown
— 3 nights
Drive:  1​h 15​min
5
Sandwich
— 2 nights
Drive:  1​h 15​min
6
Newport
— 2 nights
Fly:  4​h 45​min
End: Washington DC

3
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.
Step out of Boston to go to Salem and see The House of the Seven Gables, which is approximately 42 minutes away. There's still lots to do: explore the world behind art at Museum of Fine Arts, appreciate the extensive heritage of Freedom Trail, buy something for everyone on your list at Faneuil Hall Marketplace, and admire the natural beauty at Boston Public Garden.

To find other places to visit, traveler tips, ratings, and more tourist information, you can read our Boston route planning website .

Washington DC to Boston is an approximately 3-hour flight. You can also do a combination of train and flight; or drive. While traveling from Washington DC, expect slightly colder days and about the same nights in Boston, ranging from highs of 64°F to lows of 50°F. Finish up your sightseeing early on the 14th (Mon) so you can go by car to Ogunquit.

Things to do in Boston

Museums Historic Sites Parks

Side Trip

The House of the Seven Gables
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Freedom Trail ©
Freedom Trail

2
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.
Kick off your visit on the 15th (Tue): sample the tasty concoctions at Tributary Brewing, then visit a coastal fixture at Nubble Lighthouse, then explore the striking landscape at Perkins Cove, and finally appreciate the extensive heritage of Marginal Way Walkway. On the 16th (Wed), you'll have a packed day of sightseeing: steep yourself in history at Strawbery Banke Museum, trek along Salisbury Rail Trail, then pause for some serene contemplation at St. Ann's Episcopal Church, and finally tour the pleasant surroundings at Ogunquit Beach.

To find maps, more things to do, other places to visit, and tourist information, go to the Ogunquit trip planner.

Drive from Boston to Ogunquit in 1.5 hours. Alternatively, you can take a train; or take a bus. Plan for slightly colder nights when traveling from Boston in October since evenings lows in Ogunquit dip to 38°F. Wrap up your sightseeing on the 16th (Wed) early enough to drive to North Conway.

Things to do in Ogunquit

Historic Sites Parks Outdoors

Side Trips

Nubble Lighthouse, Strawbery Banke Museum, Tributary Brewing, Salisbury Rail Trail, St. Ann's Episcopal Church
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Nubble Lighthouse ©
Nubble Lighthouse
Perkins Cove ©
Perkins Cove

3
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.
Explore the numerous day-trip ideas around North Conway: Franconia (Flume Gorge & Franconia Notch State Park), West Rattlesnake Mountain (in Holderness) and Zipline (in Lincoln). And it doesn't end there: take a memorable drive along Kancamagus Highway, stroll around Dog Mountain Home of Stephen Huneck Gallery, hike along Rocky Gorge, and look and learn at Mount Washington Observatory Weather Discovery Center.

To see other places to visit, reviews, where to stay, and other tourist information, read our North Conway day trip app .

Traveling by car from Ogunquit to North Conway takes 2 hours. Alternatively, you can take a bus. Plan for somewhat warmer nights when traveling from Ogunquit in October since evenings lows in North Conway dip to 45°F. Finish up your sightseeing early on the 19th (Sat) so you can go by car to Provincetown.

Things to do in North Conway

Parks Outdoors Nature

Side Trips

Franconia, West Rattlesnake Mountain, Dog Mountain Home of Stephen Huneck Gallery, Rocky Gorge, Zipline
Highlights from your plan
West Rattlesnake Mountain ©
West Rattlesnake Mountain
Kancamagus Highway ©
Kancamagus Highway
Franconia Notch State Park ©
Franconia Notch State Park

3
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.
Explore Provincetown's surroundings by going to Nauset Beach (in Orleans) and Salt Pond Visitor Center (in Eastham). Next up on the itinerary: kick back and relax at Cape Cod National Seashore, see the interesting displays at Pilgrim Monument & Provincetown Museum, get up close to creatures of the deep with a dolphin and whale watching tour, and tour the pleasant surroundings at Herring Cove Beach.

To find photos, where to stay, reviews, and more tourist information, read Provincetown trip itinerary planning website .

Getting from North Conway to Provincetown by car takes about 5.5 hours. Other options: do a combination of bus and ferry; or do a combination of bus and flight. In October, daily temperatures in Provincetown can reach 63°F, while at night they dip to 49°F. Finish your sightseeing early on the 22nd (Tue) so you can drive to Sandwich.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Cape Cod National Seashore, Nauset Beach, Marconi Beach, Salt Pond Visitor Center
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Pilgrim Monument & Provincetown Museum ©
Race Point Beach ©
Race Point Beach

2
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. On the 23rd (Wed), examine the collection at Heritage Museums & Gardens, engage your brain at Sandwich Glass Museum, then tour the pleasant surroundings at Shining Sea Bikeway, and finally steep yourself in history at Plymouth Rock. Get ready for a full day of sightseeing on the next day: take an in-depth tour of Plimoth Plantation, then contemplate the long history of Mayflower II, and then kick back and relax at Chatham Lighthouse Beach.

To see photos, other places to visit, and other tourist information, use the Sandwich road trip planning app .

Drive from Provincetown to Sandwich in 1.5 hours. Alternatively, you can take a bus. October in Sandwich sees daily highs of 64°F and lows of 46°F at night. Finish up your sightseeing early on the 24th (Thu) so you can go by car to Newport.

Things to do in Sandwich

Museums Outdoors Parks

Side Trips

Plymouth, Chatham Lighthouse Beach, Shining Sea Bikeway
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation
Sandwich Glass Museum ©
Sandwich Glass Museum

2
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 25th (Fri): admire the landmark architecture of Marble House, then see the interesting displays at The Breakers, then appreciate the extensive heritage of Cliff Walk, and finally take in the architecture and atmosphere at St. Mary's Catholic Church. Here are some ideas for day two: take a memorable drive along Ocean Drive Historic District, contemplate the long history of The Elms, and then steep yourself in history at Lizzie Borden House.

To see reviews, where to stay, other places to visit, and tourist information, read our Newport tour planner.

Drive from Sandwich to Newport in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In October, plan for daily highs up to 64°F, and evening lows to 50°F. Wrap up your sightseeing on the 26th (Sat) early enough to travel back home.

Things to do in Newport

Historic Sites Outdoors Museums

Side Trip

Lizzie Borden House
Highlights from your plan
The Breakers ©
The Breakers
Ocean Drive Historic District ©
Ocean Drive Historic District
The Elms
The Elms

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