29 days in Boston, New York City & Brockton Itinerary

29 days in Boston, New York City & Brockton Itinerary

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Route & dates

29 days in Boston, New York City & Brockton Itinerary

Start: Brockton
Drive:  1​h
— 9 nights
Fly + Bus:  3​h 15​min
New York City
— 2 nights
Drive:  4​h 30​min
— 17 nights
End: Brockton


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.
Give yourself a bit of retail therapy at Brookline Booksmith and Faneuil Hall Marketplace. Explore the numerous day-trip ideas around Boston: Kittery Trading Post (in Kittery), Ogunquit (Marginal Way Walkway, Spoiled Rotten, & more) and Cape Neddick Nubble Lighthouse (in York). Next up on the itinerary: stop by Harvard Book Store, don't miss a visit to Boston Public Library, get a taste of the local shopping with Newbury Street, and admire all the interesting features of Fenway Park.

For photos, where to stay, reviews, and tourist information, use the Boston trip website .

Brockton to Boston is an approximately 1-hour car ride. Expect a daytime high around 28°C in June, and nighttime lows around 18°C. Wrap up your sightseeing on the 18th (Mon) to allow time to travel to New York City.

Things to do in Boston

Museums Parks Shopping

Side Trips

Ogunquit, Cambridge, Brookline Booksmith, Nubble Lighthouse, Kittery Trading Post
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Brookline Booksmith ©
Brookline Booksmith
Faneuil Hall Marketplace ©
Faneuil Hall Marketplace

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.
On the 18th (Mon), explore the galleries of 9/11 Memorial and then go for a walk through Central Park. Here are some ideas for day two: explore the world behind art at The Metropolitan Museum of Art and then take a stroll through Fifth Avenue.

To find where to stay, traveler tips, ratings, and more tourist information, use the New York City trip itinerary builder website .

Traveling by combination of bus and flight from Boston to New York City takes 3.5 hours. Alternatively, you can drive; or take a bus. In June, plan for daily highs up to 31°C, and evening lows to 21°C. Finish up your sightseeing early on the 20th (Wed) so you can travel to Brockton.

Things to do in New York City

Parks Museums Neighborhoods
Highlights from your plan
Central Park ©
Central Park
Fifth Avenue ©
Fifth Avenue
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art


Brockton ©
Brockton is a city in Plymouth County, Massachusetts, United States; the population was 95,314 in the 2015 Census. Head to Wrentham Village Premium Outlets and Bass Pro Shopsfor some retail therapy. Explore Brockton's surroundings by going to Sandwich (Heritage Museums & Gardens, Old King's Hwy, & more), Yarmouth Port (Captain Bangs Hallet House Museum, Edward Gorey House, & more) and Southwick's Zoo (in Mendon). The adventure continues: stroll through Corn Hill Beach, admire the majestic nature at Colt State Park, contemplate the waterfront views at Cape Cod Canal, and pick up a one of a kind souvenir at Antiques Center of Yarmouth.

To find ratings, more things to do, other places to visit, and other tourist information, read our Brockton road trip planning app .

Drive from New York City to Brockton in 4 hours. Traveling from New York City in June, things will get a bit cooler in Brockton: highs are around 28°C and lows about 16°C. Wrap up your sightseeing on the 7th (Sat) to allow time to travel back home.

Things to do in Brockton

Parks Outdoors Beaches

Side Trips

Providence, Sandwich, Yarmouth Port, Falmouth, Narragansett
Highlights from your plan
Roger Williams Park Zoo ©
Roger Williams Park Zoo
Antiques Center of Yarmouth ©
Antiques Center of Yarmouth
Wrentham Village Premium Outlets ©
Wrentham Village Premium Outlets