The Circle

The Best Activities Around Boston for Seniors

One of the best parts of independent living at Waterstone at the Circle is that you can enjoy urban living with all the conveniences of a lifestyle centered around your happiness – and this includes culturally immersive programs, carefree living, and a prime location putting you close to everything that matters to you.

Whether you simply want to enjoy all that our location offers, are looking to enjoy an activity with your grandchildren, or want to explore the range of senior-friendly activities around the Boston area, there’s an ever-growing list of things to do.

Senior-Friendly Things To Do in Boston and Beyond

At Waterstone at the Circle, and in Boston in general, there’s something for everyone to enjoy. No matter your goal or interests, we’re sure there’s an option that will bring you joy, fun and excitement. Check out some of our top suggestions below.

Take in the sports – or get some exercise.

Boston is located in the perfect place for getting active or enjoying a range of sporting activities. Whether you prefer to sit on the sidelines or get in on the action, there’s plenty to do.

  • Catch a game at Fenway Park or take a tour.
  • Enjoy time at Boston Common, America’s oldest public park.
  • Stroll along the Chestnut Hill Reservoir.
  • Visit one of the many gardens throughout our area.
  • Go golfing in Boston’s surrounding area.
  • Swim, kayak or build sandcastles with the grandkids on some of the many accessible islands.

Tour historic sites and national historic landmarks.

Are you a history lover? You’ve come to the right place! There are so many historical sites to enjoy. Consider visiting one of these or enjoying a guided tour!

  • Visit the Paul Revere House or see if an event is scheduled soon.
  • Tour the USS Constitution or visit the museum.
  • Check out the old churches and their beautiful stained-glass pieces throughout Boston.
  • Take a trolley tour.
  • Check out the Bunker Hill Monument when it re-opens! It’s been receiving ongoing restoration work as of March 28, 2022.
  • Visit one of the many educational institutions in the area, like Harvard University or Boston College.
  • Book a guided walking tour on the Freedom Trail.

Delight in dining.

There’s never a shortage of delicious dining options in Boston. Whether you are looking for fine dining or something more casual, these options may do the trick.

  • Grab some delicious seafood at the Boston Harbor.
  • Visit the North End for Italian food.
  • Check out one of the many food trucks you can usually find.
  • Enjoy outdoor dining at one of many beautiful locations throughout Boston.
  • Visit some of the breweries, wineries and more in the area.
  • Enjoy some of the best area dishes with a Yummy Walks guided food tour.

Go shopping.

For some, there’s nothing more fun than finding a new favorite shop, supporting local businesses or enjoying quality time having fun shopping with friends. Boston is full of wonderful places to shop ‘til you drop! Visit:

  • Visit Faneuil Hall Marketplace.
  • Shop name brands at Copley Place.
  • Check out the vendors at Haymarket Boston.
  • Shop at the Prudential Center.
  • Visit The Street in Chestnut Hill.

Explore on the water.

Do you and your friends love to set sail? Boston and the surrounding area are great places to start. Try some of these ideas to satisfy your love of the water.

  • Did you know that May through October is the best time for whale watching? Consider booking a tour.
  • Take a ride in a swan boat in the public garden lagoon.
  • Make a splash with a Boston Duck Tour, crossing both land and water.
  • Go fishing for bass.
  • Check out the Charles River Watershed, which begins in Hopkinton and ends in the Boston Harbor.

Visit popular attractions.

Whether your grandkids are visiting, your friends are coming to stay for a bit, or you simply want to explore, some of these popular attractions might just be what you’re looking for!

Something for everyone.

As you can see, there are plenty of things for seniors to do in the Boston and Chestnut Hill areas. What’s even better is that, at Waterstone at the Circle, we put you in the center of it all.

Situated at the intersection of Chestnut Hill Avenue and Beacon Street, Waterstone at the Circle’s landmark location puts you near shopping, dining, entertainment, cultural venues and more.

Enjoy any of the above activities by taking public transportation, driving yourself or taking advantage of our chauffeur and concierge services, or simply enjoy everything our community has to offer. From fine dining to engaging programs, social opportunities and more, there is always something to enjoy at our luxury retirement community.

Before you set off.

As we all know in these times, shops may close, restaurants may limit seating, shows may have requirements, and hours may vary. Make sure that when you are considering your plans, you call, visit social media pages, or check out their websites prior to your planning and arrival. This can ensure these attractions are open to the public while preventing any unwanted changes in plans or disappointments.

Also, be sure to check out wheelchair accessibility, if needed, and consider the weather before you go if planning an event outdoors!


For more information about Waterstone at the Circle, Boston’s premier independent living community for seniors 62 and over, contact us today.