The Circle

The Best Scenic Drives in Boston

The air is getting cooler, the leaves are beginning to change, and there’s a hint of festivity in the air. This can only mean one thing – fall is on its way.

Whether you’re most excited about the pumpkin-flavored and seasonally scented goods, the ability to break out your coziest clothes and blankets, or the ever-stunning fall foliage drives for leaf peeping, Boston is among the best places to be.

If you’re ready to leaf summer behind and welcome autumn with festive flair, we’re here to help. Check out some of the best fall drives in Boston, MA, with our list below.

bridge in boston in the fall

Drive Around Boston Common – Then Have a Picnic

There are plenty of beautiful fall colors to see throughout Boston Common. Take a drive around the perimeter or park and go for a walk. If you decide to take off by foot, consider exploring the public garden.

Take the Scenic Route Along the Charles River

Take Memorial Drive in Cambridge to see the foliage of Boston over the Charles River. If you prefer to ride your bike, ride along the Charles River Esplanade.

Want to see the foliage from a different perspective? Try a fall foliage sightseeing cruise.

Arnold Arboretum in Boston in the sunset

Drive (or Walk!) Around Arnold Arboretum

Harvard’s Arnold Arboretum is a great place to leaf peep! Explore the 281-acre landscape by foot or drive along the roads to enjoy a brief look of all the colors.

Travel Along Freedom Trail®

Take in a little history during this gorgeous season by stopping along historical sites on the Freedom Trail®. As you travel to each stop, you’ll see stunning views while enjoying the opportunity to learn.

Go Beyond Boston

If you’re looking to go outside of Boston, try the Mohawk Trail, Walden Pond, Jacob’s Ladder Scenic Byway, and the Kancamagus Highway, a national scenic byway in the White Mountain National Forest.

fall drive down a highway

A Prime Location for Lovers of Autumn

Although our location makes traveling to national historic parks and state parks simple, it’s also possible to enjoy the beautiful foliage right from our community.

Beautiful views can be seen from many spots within our doors, including the balcony of the fifth-floor lounge. Whether you want to view the foliage from Cassidy Park from inside Waterstone at the Circle, or you’d prefer to get some exercise with a short walk to Chestnut Hill Reservoir, we’ll easily meet your preference. Then, when you’re all done, savor a nice cup of coffee or tea and cozy in knowing you can simply enjoy the season as you please.

There’s nothing like autumn in New England, and no senior living experience like Waterstone at the Circle. Call us today at 617.396.4422 to schedule a visit to our beautiful community.