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.
Following the Berkshire Cheese Trail
Northeast Farm Tours Let Visitors Connect With the Land
Cape Cod Drive Reinforces Benefits of Slow Travel
Rockport, Massachusetts, is a Relaxing, Seaside Getaway
A Bayou Writer Goes Maple Sugaring in New England
Artsy Provincetown Offers an Inclusive Getaway
Get more Massachusetts road trip ideas.
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!
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.
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.