18 days in New York City, Berkshires & Boston Itinerary

18 days in New York City, Berkshires & Boston Itinerary

Created using Inspirock United States itinerary planner

This plan was created by another user.  Make it your plan

Route & dates

18 days in New York City, Berkshires & Boston Itinerary

Start: London
Fly:  10​h 45​min
1
New York City
— 7 nights
Drive:  3​h 45​min
2
Charlemont
— 3 nights
Drive:  1​h 30​min
3
Stockbridge
— 3 nights
Drive:  2​h 30​min
4
Boston
— 3 nights
Fly:  9​h 45​min
End: London

7
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.
9/11 Memorial and St. Patrick's Cathedral will appeal to history buffs. For shopping fun, head to Fifth Avenue or Strand Bookstore. Take a break from New York City with a short trip to Woodbury Common Premium Outlets in Central Valley, about 1h 10 min away. The adventure continues: browse the exhibits of The Metropolitan Museum of Art, see the interesting displays at New York Public Library, contemplate the long history of Ellis Island, and get a taste of the local shopping with Shopping Girlfriend NYC.

To see traveler tips, other places to visit, reviews, and more tourist information, use the New York City attractions planner.

London, UK to New York City is an approximately 11-hour combination of flight and bus. You can also do a combination of flight and train. The time zone changes from Greenwich Mean Time to Eastern Standard Time, which is usually a -5 hour difference. Plan for a bit warmer temperatures traveling from London in August, with highs in New York City at 34°C and lows at 26°C. Finish up your sightseeing early on the 22nd (Wed) so you can travel to Charlemont.

Things to do in New York City

Museums Shopping Parks

Side Trip

Woodbury Common Premium Outlets
Highlights from your plan
9/11 Memorial ©
9/11 Memorial
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
New York Public Library ©
New York Public Library

3
nights
Charlemont

Charlemont ©
Charlemont is a town in Franklin County, Massachusetts, United States. Let the collections at Clark Art Institute and Williams College Museum of Art capture your imagination. Eschew the tourist crowds and head to Franklin Pierce Homestead and Ava Marie Handmade Chocolates. Venture out of the city with trips to North Adams (Windsor Lake & MASS MoCA), Williamstown (Sweet Brook Farm & Williams College) and Unbridled Chocolates (in Keene). There's still lots to do: look for gifts at A.L. Avery & Son General Store and admire the majestic nature at Mohawk Trail State Forest.

For where to stay, more things to do, photos, and tourist information, read Charlemont online trip builder .

Getting from New York City to Charlemont by car takes about 3.5 hours. Traveling from New York City in August, expect Charlemont to be little chillier, temps between 30°C and 16°C. Wrap up your sightseeing on the 25th (Sat) early enough to travel to Stockbridge.

Things to do in Charlemont

Parks Nature Shopping

Side Trips

Williamstown, North Adams, Ava Marie Handmade Chocolates, Unbridled Chocolates, Franklin Pierce Homestead State Historic Site
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
MASS MoCA ©
MASS MoCA

3
nights
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Kick off your visit on the 26th (Sun): view the masterpieces at Schantz Galleries, then examine the collection at Frelinghuysen Morris House & Studio, then stop by The Bookstore, and finally get some fabulous bargains at Lee Premium Outlets. Get ready for a full day of sightseeing on the next day: explore the world behind art at Norman Rockwell Museum, then steep yourself in history at Chesterwood Museum, then stop by Museum Facsimiles Outlet Store, and finally stop by Guido's Fresh Marketplace.

To find ratings, traveler tips, reviews, and other tourist information, refer to the Stockbridge vacation planner .

Getting from Charlemont to Stockbridge by car takes about 1.5 hours. In August, daytime highs in Stockbridge are 30°C, while nighttime lows are 16°C. Finish your sightseeing early on the 28th (Tue) so you can drive to Boston.

Things to do in Stockbridge

Shopping Museums Historic Sites

Side Trips

Lenox, Pittsfield, Lee Premium Outlets
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Schantz Galleries ©
Schantz Galleries
Frelinghuysen Morris House & Studio ©

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.
For shopping fun, head to Faneuil Hall Marketplace or When Pigs Fly Company Store. You'll discover tucked-away gems like Marginal Way Walkway and Cliff Walk. Get out of town with these interesting Boston side-trips: Newport (The Breakers & Ocean Drive Historic District), Fantastic Umbrella Factory (in Charlestown) and Cape Neddick Nubble Lighthouse (in York). Next up on the itinerary: wander the streets of North End, go for a walk through Quincy Market, and make a trip to Louisburg Square.

To find where to stay, reviews, and tourist information, read our Boston trip itinerary site .

Traveling by car from Stockbridge to Boston takes 2.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Stockbridge in August, plan for a bit warmer nights in Boston, with lows around 22°C. Finish your sightseeing early on the 31st (Fri) to allow enough time to travel back home.

Things to do in Boston

Historic Sites Outdoors Shopping

Side Trips

Newport, Marginal Way Walkway, When Pigs Fly Company Store, Nubble Lighthouse, Fantastic Umbrella Factory
Highlights from your plan
North End ©
North End
Marginal Way Walkway ©
Marginal Way Walkway
The Breakers ©
The Breakers

Similar Plans

21 days in New York City BY A USER FROM GEORGIA November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 20 days in New York City, Orlando & Miami BY A USER FROM BAHRAIN December, outdoors, relaxing, romantic, beaches, shopping, wildlife, popular & hidden gems PREFERENCES: December, outdoors, relaxing, romantic, beaches, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 21 days in New York City BY A USER FROM NETHERLANDS July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 22 days in United States BY A USER FROM AUSTRALIA December, culture, outdoors, relaxing, romantic, beaches, museums, shopping, wildlife, popular sights PREFERENCES: December, culture, outdoors, relaxing, romantic, beaches, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 16 days in New York City BY A USER FROM PORTUGAL June, teens, outdoors, relaxing, romantic, beaches, shopping, wildlife, hidden gems PREFERENCES: June, teens, outdoors, relaxing, romantic, beaches, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 22 days in New York City & Los Angeles BY A USER FROM RUSSIA June, outdoors, relaxing, beaches, historic sites, popular sights PREFERENCES: June, outdoors, relaxing, beaches, historic sites ATTRACTION STYLE: Popular sights PACE: Medium 47 days in New York City BY A USER FROM INDIA December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 22 days in Florida & New York City BY A USER FROM AUSTRALIA November, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular sights PREFERENCES: November, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 19 days in United States BY A USER FROM SOUTH AFRICA March, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular sights PREFERENCES: March, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 29 days in New York City BY A USER FROM SLOVENIA August, culture, outdoors, relaxing, romantic, beaches, wildlife, popular sights PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 37 days in New York City BY A USER FROM MALAYSIA November, relaxing, beaches, historic sites, wildlife, slow & easy, popular sights PREFERENCES: November, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy
View more plans