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!


Massachusetts Road Trips



Massachusetts Road Trip Inspiration


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.

Yoga Retreats of the Northeast

Legendary resorts ensure a relaxing journey.

Massachusetts Trips

Plan your next road trip, weekend getaway or personal challenge.

Cape Cod Drive Reinforces Benefits of Slow Travel

Cape Cod’s laidback vibe is apparent when you steer your Enterprise rental car along historic Massachusetts State Route 6A, a road less traveled that offers quality time. Relax on the National Seashore, explore charming towns and enjoy fresh oysters at every stop.

Following the Berkshire Cheese Trail

Head to Northeast dairy country for some of America’s finest cheeses.
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Northeast Farm Tours Let Visitors Connect With the Land

People are discovering the origins of their food.
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Looking for more road trip ideas? Check out our Road Trip Planner and choose your next journey!

Road Trip Ideas

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