Massachusetts Trips

What Inspires You?

Beaches ▪ Family ▪ Food ▪ Haunted ▪ Music ▪ National Parks ▪ Outdoor Adventures ▪ Relaxation ▪ Road Trips ▪ Scenic Drives ▪ Shopping ▪ Space ▪ Weekend Getaways

Destinations: Trips by State or Province ▪ Northeast ▪ South ▪ Midwest ▪ West ▪ Canada ▪ Mexico
Seasons: Spring ▪ Summer ▪ Fall ▪ Winter

Immerse yourself in history in Plymouth. In Boston, chow down on a lobster roll. Go whale-watching from the tip of Cape Cod. Visit Berkshire County to sample fresh-tapped maple sugar. Walk the beaches on Martha’s Vineyard or explore cobblestone streets on Nantucket Island. Let Enterprise Rent-A-Car help you do all that for a romantic getaway or a vacation with the family.

Yoga Retreats of the Northeast

Legendary resorts ensure a relaxing journey.

Cape Cod Drive Reinforces Benefits of Slow Travel

Massachusetts oyster farmers also recognize the value of investing time.

Road Trip to Maple Sugar Shacks in New England

From New Orleans to the Northeast, one foodie sets out to explore the sweet beyond.

Artsy Provincetown Offers an Inclusive Getaway

Everyone is welcome in this Massachusetts beach town.

Rockport, Massachusetts, is a Relaxing, Seaside Getaway

The quaint town offers a bounty of seafood, a scenic shoreline and even a house made of paper.

Following the Berkshire Cheese Trail

Head to Northeast dairy country for some of America’s finest cheeses.

People are discovering the origins of their food.

Get more Massachusetts road trip ideas.

Historic Drive from Philadelphia to Boston

Filled with American history around every turn, the drive from Philadelphia to Boston is fun, intriguing, and offers plenty of things to see and do. Pick up a rental vehicle and enjoy this scenic road trip.

Drive from New York to Boston

Hop in the car and drive from New York to Boston. Discover interesting stops along short drive from the Big Apple to Beantown.

Boston to Maine Road Trip

Explore the Northeastern U.S. on this road trip from Boston to Bar Harbor, where you'll find a unique mix of history and awesome scenery along the way.

Day Trip from Boston to Cape Cod and Beyond

Discover some of the best scenery the East coast has to offer on a road trip from Boston to Cape Cod. Book an Enterprise rental car to visit all the best stops along the way!

Road Trip from Boston to New York City

Explore Bristol, New Haven and more as you drive from Boston to New York City using this weekend trip itinerary.

Massachusetts Road Trips

In the heart of New England, Massachusetts is a perfect place to start any road trip. Boston is a fun town filled with historical significance, great food, professional sports and things to do. From there, great destinations in numerous states are merely a few hours away. Take a ride with Enterprise Rent-A-Car and start your journey from Massachusetts today!

Drive From New York City to Nantucket

Looking to go from New York City to Nantucket? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.

New York City to Cape Cod

Looking to go from New York City to Cape Cod? Driving may be your best option. Our neighborhood locations are open and ready to serve you with curbside pickup and modified cleaning procedures.