Road Trip from Boston to NYC

Day 1: Start off your trip by taking a two-hour drive from Boston to Bristol, covering 120 miles on I-90 W and I-84.
 

Rent a Car at Boston Airport

This gem of a town is packed with charming highlights. Take in a bit of local history with a stroll through the American Clock & Watch Museum housed in an 1801 Federal-style house. If the weather's nice, head to Hoppers Birge Pond and Nature Preserve and explore some of the walking and hiking trails. Stop for lunch at Greer's Chicken, where you'll find the best fried chicken in town. Take-out is available if you'd prefer a picnic.

Check the schedule at the Memorial Boulevard Theatre and The Ingraham House for an evening of live entertainment. Both are historic venues that are fascinating attractions all on their own, making their performances decadent icing on the cake. Head to 457 Mason Jar for a filling dinner. The extensive menu has something for every taste, including Maple Thyme Salmon Filet, Cajun Rubbed Catfish, and Filet Mignon.

Day 2: The charming city of New Haven sits in stark contrast to the glitz of New York City, making it the perfect place to rest up on your road trip. You can cover the 38 miles to New Haven from Bristol in about 46 minutes via I-91 S. The Yale University Art Gallery is the oldest university art museum in the country, featuring everything from Egyptian pieces to contemporary paintings. Enjoy a quiet, contemplative morning taking in the museum's highlights. After lunch, head to the Peabody Museum of Natural History for fascinating exhibits like the Great Hall of Dinosaurs.

Visit the August Upscale Bar and Eatery for a romantic dinner in the wine bar's cozy space. A simple one-page menu ensures that every selection is exquisite. End your day with a sunset stroll through Lighthouse Point Park to see the park's famous antique carousel alongside stunning views of the harbor.

Day 3: You'll reach New York City in just under two hours, covering the 86 miles from New Haven via CT-15 S. Complete your romantic getaway with a picturesque stroll through the Brooklyn Botanic Garden. Browse the delights of the Chelsea Market hand-in-hand for a leisurely activity, or head to the high-energy Brooklyn Night Bazaar, with its arcade games, karaoke rooms and mini-golf.

Turn your New York City vacation from a destination-focused trip to one that's all about the journey. Slow down along the way and you can enjoy a diverse range of highlights from fine dining to fascinating museums at numerous cities along your route. Just pack up the car and start your adventure.

Rent a Car in New York City

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Boston to New York Road Trip FAQs

Are there toll roads between Boston and NYC?

Interstate 90, the Massachusetts Turnpike, is a toll road. Traveling from downtown Boston to the Interstate 84 interchange (Exit 9) will cost you $4.15 in toll fees. No tolls exist along Interstate 84 and Interstate 95, so you won't have to pay any fees until you reach New York City. Note that tolls in Massachusetts don't accept cash payments, so you'll want to get an EZPass transponder or account. If you're traveling from Bronx to Queens, you'll probably use the Whitestone Bridge or Throgs Neck Bridge. The toll fees at these two locations are $8.50 by mail and $5.76 with EZPass (as of January 2019).
 

How do I navigate toll roads and bridges in New York?

Tolls in New York City can get expensive. You can use Google Maps or a GPS app to help identify alternate routes without toll roads. If you must use toll roads, consider investing in an EZPass. 

Some bridges in New York City charge considerable tolls, so try to use toll-free bridges when possible, such as the Brooklyn Bridge, Manhattan Bridge, or Williamsburg Bridge. 

Where should I park in New York City?

Many drivers in New York City use parking garages and outdoor parking lots, as street parking can be sparse. You can look online for garages and parking lots that offer the best rates and book a space before you arrive at your destination. If you want to save more money on parking, consider parking somewhere farther from the city center and take the subway to your destination.
 

Where should I stop along the East coast?

• Boston, MA
• Bristol, CT
• New Haven, CT
• New York City, NY

What type of rental car should I reserve for this trip?

Since you'll be driving on interstate highways almost the entire trip, you can expect to have an easy and pleasant journey whether you use a sedan or SUV. If you have more than two passengers traveling with you, an SUV would be the best choice, as it provides additional room.  

When is the best time of year to drive to New York?

The best time to take the drive from Boston to New York City is from September to early November. The weather is enjoyable and the tourist crowds are less overwhelming. The New England region is known for its fall foliage, which also makes for a scenic drive. 

Between summer and early fall, the region can experience considerable rainfall and sometimes thunderstorms. Be sure to check the weather before hitting the road. 

If you’re traveling in winter months, be careful of ice and snowy conditions. Use precautions and rent an all-wheel drive vehicle if possible. 

Are there any kid-friendly activities along the way?

Many kid-friendly attractions and activities exist between Boston and New York City. In Bristol, your children can enjoy interactive play at the Imagine Nation, view modern and historic merry-go-round equipment at the New England Carousel Museum, and indulge in sweet treats at the It! Candy store and Frozen Delights. 

New Haven also has many great attractions for children, including the IT Adventure Indoor Ropes Course, Escape New Haven, Arethusa Farms, Connecticut Children's Museum, and the Leitner Family Observatory and Planetarium. If you're stopping over in Norwalk, bring your kids to the Stepping Stones Museum for Children, Sheffield Island Lighthouse, and the SONO Field House. 

Where should I eat in Bristol, Connecticut?

For breakfast, you can savor a hearty American-style meal at 457 Mason Jar, enjoy a fresh bagel sandwich at the New York-style Bagels Plus Deli, or eat healthy at the vegetarian-friendly Parkside Cafe. For lunch, make your way to Greer's Chicken for a mouth-watering fried chicken meal, Monterrey Mexican Restaurant for authentic Mexican food, or San Gennaro Napolitano Pizza for wood-fired pizza. 

For an elegant dinner experience, head to the Willows Restaurant, which offers innovative American dishes and excellent wine pairings. If you're craving fresh seafood or a steak, Cava Restaurant in nearby Southington is recommended.