37 days in United States Itinerary

37 days in United States Itinerary

Created using Inspirock United States attractions planner

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Route & dates

37 days in United States Itinerary

Start: New York City
1
New York City
— 21 nights
Drive:  3​h
2
Stockbridge
— 2 nights
Drive:  3​h
3
Newport
— 2 nights
Drive:  2​h 45​min
4
Provincetown
— 2 nights
Fly:  5​h 30​min
5
Bar Harbor, Mount Desert Island
— 2 nights
Drive:  4​h 30​min
6
North Conway
— 2 nights
Drive:  2​h
7
Ogunquit
— 2 nights
Drive:  1​h 30​min
8
Boston
— 3 nights
Fly + bus:  3​h
End: New York City

21
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Brooklyn Bridge has been added to your itinerary. Discover out-of-the-way places like The Met Cloisters and Independence National Historical Park. Your inner history buff will appreciate Brooklyn Heights Promenade and 9/11 Memorial. Get out of town with these interesting New York City side-trips: Edwin B. Forsythe National Wildlife Refuge (in Oceanville), Cornelia & Florence Bridge Nature Preserve (in Milford) and Philadelphia (Independence Hall, Eastern State Penitentiary, & more). Next up on the itinerary: browse the exhibits of The Metropolitan Museum of Art, take in the pleasant sights at Central Park, wander the streets of Times Square, and indulge in some culinary diversions at a local gastronomic tour.

Plan trip to New York City with our itinerary maker to find out where to go and what to do.

If you are flying in from Netherlands, the closest major airports are La Guardia Airport, Newark Liberty International Airport and John F Kennedy International Airport. Expect a daytime high around 31°C in September, and nighttime lows around 22°C. Finish up your sightseeing early on the 22nd (Tue) so you can go by car to Stockbridge.

Things to do in New York City

Parks Wildlife Museums

Side Trips

Philadelphia, Brooklyn, Wallace House and Old Dutch Parsonage, Meschutt Beach, Fort Montgomery State Historic Site
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Independence National Historical Park ©
The Met Cloisters ©
The Met Cloisters

2
nights
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Start off your visit on the 23rd (Wed): admire the masterpieces at Norman Rockwell Museum, then admire the natural beauty at Berkshire Botanical Garden, and then steep yourself in history at Chesterwood Museum. Get ready for a full day of sightseeing on the next day: steep yourself in history at Herman Melville's Arrowhead, stop by Williams & Sons Country Store, then take in the exciting artwork at Schantz Galleries, then admire the natural beauty at Naumkeag, and finally take in the spiritual surroundings of National Shrine of the Divine Mercy.

To see photos and other tourist information, read Stockbridge attractions planning site .

Getting from New York City to Stockbridge by car takes about 3 hours. Other options: take a bus. In September, Stockbridge is slightly colder than New York City - with highs of 26°C and lows of 11°C. Finish your sightseeing early on the 24th (Thu) so you can drive to Newport.

Things to do in Stockbridge

Historic Sites Parks Museums

Side Trip

Herman Melville's Arrowhead
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Chesterwood Museum ©
Chesterwood Museum
National Shrine of the Divine Mercy ©

2
nights
Newport

Newport
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Kick off your visit on the 25th (Fri): contemplate the long history of Touro Synagogue, steep yourself in history at Kingscote, then see the interesting displays at Audrain Automobile Museum, then steep yourself in history at The Elms, and finally pause for some serene contemplation at St. Mary's Catholic Church. Get ready for a full day of sightseeing on the next day: explore the galleries of Chepstow, then take a memorable drive along Ocean Drive Historic District, then enjoy the sea views from Castle Hill Lighthouse, and finally enjoy the sea views from Rose Island Lightouse.

For traveler tips, where to stay, more things to do, and other tourist information, read our Newport trip planning tool .

You can drive from Stockbridge to Newport in 3 hours. Other options are to take a bus; or do a combination of bus and train. Traveling from Stockbridge in September, expect somewhat warmer with lows of 17°C in Newport. Finish your sightseeing early on the 26th (Sat) so you can drive to Provincetown.

Things to do in Newport

Historic Sites Museums Scenic Drive
Highlights from your plan
The Elms
The Elms
Ocean Drive Historic District ©
Ocean Drive Historic District
Touro Synagogue ©
Touro Synagogue

2
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.
Start off your visit on the 27th (Sun): steep yourself in history at Chatham's Godfrey Windmill, then appreciate the extensive heritage of Fort Hill Rural Historic District, then enjoy the sand and surf at First Encounter Beach, and finally get to know the fascinating history of Wellfleet Bay Wildlife Sanctuary. Keep things going the next day: stroll through Province Lands Bike Trail, enjoy the sea views from Wood End Lighthouse, then indulge in some personalized pampering at some of the best spas, and finally pause for some photo ops at Pilgrim Monument & Provincetown Museum.

To see maps, ratings, and tourist information, read our Provincetown day trip planning site .

You can drive from Newport to Provincetown in 3 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of train and ferry. September in Provincetown sees daily highs of 25°C and lows of 16°C at night. Wrap up your sightseeing on the 28th (Mon) early enough to travel to Bar Harbor.

Things to do in Provincetown

Historic Sites Parks Outdoors

Side Trips

Eastham, Wellfleet Bay Wildlife Sanctuary, Chatham's Godfrey Windmill
Highlights from your plan
Fort Hill Rural Historic District ©
Fort Hill Rural Historic District
Wellfleet Bay Wildlife Sanctuary ©
Wellfleet Bay Wildlife Sanctuary

2
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. On the 29th (Tue), take in the pleasant sights at Compass Harbor Trail, look for gifts at The Christmas Vacation Shop, get a new perspective on nature at George B. Dorr Museum of Natural History, take in the spiritual surroundings of St. Saviour's Church :, then indulge your thirst for a good beer at Atlantic Brewing Company, and finally enjoy the sea views from Egg Rock Light. On the 30th (Wed), you'll have a packed day of sightseeing: trek along Ocean Path, then take in the dramatic natural features at Otter Cliff, and then tour the pleasant surroundings at Cadillac Mountain North Ridge Trail.

For traveler tips, photos, where to stay, and tourist information, read our Bar Harbor trip itinerary builder .

Traveling by flight from Provincetown to Bar Harbor takes 5.5 hours. Alternatively, you can drive; or do a combination of ferry and bus. Traveling from Provincetown in September, Bar Harbor is slightly colder at night with lows of 13°C. Finish up your sightseeing early on the 30th (Wed) so you can go by car to North Conway.

Things to do in Bar Harbor

Parks Trails Outdoors

Side Trip

Otter Cliff
Highlights from your plan
Otter Cliff ©
Otter Cliff
Egg Rock Light ©
Egg Rock Light
St. Saviour's Church : ©
St. Saviour's Church :

2
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.
On the 1st (Thu), see the sky in a new way at Mount Washington Observatory Weather Discovery Center, have fun and explore at MWV Children's Museum, look for gifts at Bavarian Chocolate Haus, then identify plant and animal life at Dahl Wildlife Sanctuary, and finally take in the dramatic natural features at Black Cap Hiking Trail. Get ready for a full day of sightseeing on the 2nd (Fri): walk around Schouler Park, explore and take pictures at Cathedral Ledge, then admire the sheer force of Diana's Baths, and finally snap pictures at Honeymoon Bridge.

To find reviews and more tourist information, refer to the North Conway planner .

Drive from Bar Harbor to North Conway in 4.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of bus and car. In September, plan for daily highs up to 24°C, and evening lows to 14°C. Finish up your sightseeing early on the 2nd (Fri) so you can go by car to Ogunquit.

Things to do in North Conway

Parks Nature Childrens Museums

Side Trip

Honeymoon Bridge
Highlights from your plan
Cathedral Ledge ©
Cathedral Ledge
Diana's Baths ©
Diana's Baths
Black Cap Hiking Trail ©
Black Cap Hiking 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.
On the 3rd (Sat), get to know the fascinating history of Marginal Way Walkway, explore the world behind art at Ogunquit Museum of American Art, then get advice or help at Ogunquit Memorial Library, then look for gifts at Spoiled Rotten, and finally view the masterpieces at Abacus. Get ready for a full day of sightseeing on the 4th (Sun): appreciate the extensive heritage of Cliff Walk, then visit a coastal fixture at Portland Breakwater Lighthouse, then shop like a local with PANACHE FINE JEWELRY AND ART GALLERY, and finally take in the dramatic natural features at Perkins Cove.

To find reviews, photos, traveler tips, and other tourist information, read our Ogunquit trip builder app .

Drive from North Conway to Ogunquit in 2 hours. Alternatively, you can take a bus. Traveling from North Conway in October, plan for slightly colder nights in Ogunquit, with lows around 3°C. Finish your sightseeing early on the 4th (Sun) to allow enough time to drive to Boston.

Things to do in Ogunquit

Historic Sites Museums Shopping

Side Trips

Cliff Walk, Portland Breakwater Lighthouse
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Perkins Cove ©
Perkins Cove
Portland Breakwater Lighthouse ©
Portland Breakwater Lighthouse

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.
Kick off your visit on the 5th (Mon): get to know the fascinating history of HarborWalk, don't miss a visit to Scituate Lighthouse, steep yourself in history at Hoxie House, then get engrossed in the history at Jenney Museum, and finally immerse yourself in nature at National Monument to the Forefathers. On the next day, steep yourself in history at Louisa May Alcott's Orchard House, steep yourself in history at Buckman Tavern, contemplate the long history of Hancock-Clarke House, take in the history at Lexington Green, then take an in-depth tour of Old State House, and finally contemplate the long history of Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill.

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

Traveling by car from Ogunquit to Boston takes 1.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Ogunquit in October, Boston is a bit warmer at night with lows of 11°C. On the 7th (Wed), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Boston

Historic Sites Museums Nature

Side Trips

Lexington, Plymouth, Scituate Lighthouse, Louisa May Alcott's Orchard House, Saugus Iron Works
Highlights from your plan
Scituate Lighthouse ©
Scituate Lighthouse
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House
Old State House ©
Old State House

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