9 Best Outdoor Activities In Boston, Massachusetts - Updated 2024

Anne
Contributing Writer
Updated
| 4 min read

Boston is the capital of Massachusetts and a historic and interesting city to visit. Well known from the sitcom, Cheers, among Boston’s many attractions are Fenway Park, the Boston Common, the Freedom Trail, with its historic sites and museums, and the historic Faneuil Hall Marketplace, an indoor and outdoor shopping center. The city is known for its culture, including the Museum of Fine Arts with its Egyptian treasures and impressionist art, and the Museum of Science. Families enjoy the New England Aquarium in town, with its more than 2,000 marine animals on display, or relaxing in the fresh air in the 19th-century Boston Public Garden. Along the way, visit Boston Harbor with its iconic lighthouse and sailing trips. When visiting in the warmer months, take advantage of these outdoor activities in Boston, Massachusetts.

Why Trust Trip101?


Over 50,000 articles reviewed and published by our experienced team

Over 50 years of combined experience researching, writing and reviewing travel articles

Over 40,000 hours spent on research and fact-checking from credible sources (last year’s data)

Optimizing content from data-driven insights collected directly from users on our platform

Focus on authentic and up-to-date information by collaborating with local guides, global travelers and other industry experts

Long-standing partnerships with credible brands like Airbnb, Booking.com, Agoda, Expedia, GetYourGuide, Viator, RVShare and more

Full disclosure on any partnerships or sponsored content

Trip101’s team of writers, editors, and content managers oversees the publication of all travel content, including destination guides, accommodation recommendations, and travel tips. They have extensive experience in the travel industry and no content, written or visual, gets published without a review. Many of our team’s work has also been featured in Travel+Leisure, National Today, The Indian Express, The Telegraph (India), Robb Report, The Adventure Handbook, Tripoto, Korea Tourism Organization, and Korean Ministry of Culture, Sports and Tourism. Some of them are also members of professional organizations like the Society of American Travel Writers and the International Travel Writers and Photographers Alliance.

Each member of the team follows Trip101's methodology and strict editorial guidelines to ensure accuracy, authenticity, and relevance.

1. Exciting two-hour sail from Boston Harbor

Climb on board at Boston Harbor and don your life jacket for an enjoyable sail on a sailboat. Enjoy the fresh breeze as you explore historic Boston Harbor on the water. While onboard, take the helm while learning how to steer the boat, or just relax and enjoy the city views. Landmarks in view include the Zakim Bridge, The Tobin Bridge, Boston TD Garden, East Boston and the North End. The sailboat fits up to four adults or two adults and two children. Make sure you dress for the weather, in case it gets chilly while out on the water or it starts to rain.

Visited this place?

2. Enjoy a thrilling run through historic Boston

Keep up your exercise regimen in a fun way, while enjoying a run through historic Boston. Start off in the Boston Public Garden, then run through Boston Common and into the Beacon Hill neighborhood. Then head out along the Charles River Esplanade into Back Bay. Along the way, learn about the hidden secrets of Boston and its history, along with insights into Boston’s well-known running scene. Pass the Boston Marathon finish line before ending the run in charming South End where you will relax and enjoy a coffee.

Visited this place?

3. Take a fun hike in the Boston Harbor Islands

Meet up at Long Wharf in downtown Boston and take a ferry ride out to Spectacle Island to explore the Boston Harbor Islands National Recreation Area. During the 30-minute ferry ride, learn about the history of the islands. When arriving on Spectacle Island, take a hike to the highest point on the island to take in the fabulous views of the harbor and downtown Boston. Snacks are supplied and after the tour, take the ferry back to Long Wharf. The tour includes roundtrip ferry tickets.

Visited this place?

4. Experience a classic New England hike with spectacular views

Meet up across from Ashmont/Peabody Square T station on the Red Line of the subway and then take a stroll through Blue Hills Reservation, south of the city, to view the dense forest and stunning views over the Boston skyline. The hike takes you through quiet wooded areas and will head to two different viewpoints over the city. While it may feel like you are out in the countryside, you will be just 20 minutes from downtown Boston. For those who enjoy the fall foliage, the best time to capture the colors on this hike is between September and November.

Visited this place?

Boston Tour Guide

Naim Benmayor

Naim Benmayor

As a Boston tour guide, I have the added experience of being a world traveler. For many years, I frequently visited Europe, Asia, and Latin America on business. During this time, I also organized tours of the USA, Europe and Asia for my business clients. I now bring this passion, excitement and expertise to the Boston area.By exploring the globe, I was exposed to various cultures, and this uniq... Read more

5. Have fun on a bike ride through Boston's neighborhoods

One of the best ways to experience Boston’s neighborhoods is on a bike ride. You will head through the city using paths and bike lanes while stopping off at various attractions along the way. Learn about Boston’s unique history, passing places like Fenway Park, North End, The Charles River Esplanade, Boston University Campus, Kenmore Square, Copley Square and the finish line of the Boston Marathon, Boston Common, the Rose Kennedy Greenway, the Long Wharf and past the beautiful brownstones of Back Bay and South End.

Visited this place?

6. Learn about the game of rugby in the park

learn about the game of rugby in the park
Source: www.airbnb.com

Suitable for groups of up to 10 people, this experience will allow you to learn about the rules, teams and history of the iconic game of rugby. You will have a quick, 20-minute training session before playing a game of touch, some passing games and generally having lots of fun. This session is a fun way to meet new people and gain your host’s expertise on the game of rugby.

Visited this place?

Book Tours : Rugby in the Park

7. Participate in a fun scavenger hunt in Boston Civic Center

A fun way to explore downtown Boston is a tourist scavenger hunt that will take participants from Old City Hall through to the New England Aquarium via the Boston Commons, Faneuil Hall and Massachusetts State House. Along the way, you will solve challenges in every step of the hunt to find out your next location. You will learn history along the way, including interesting tidbits about your surroundings.

Visited this place?

8. Learn how to scuba dive

For those who have always wanted to scuba dive, these diving lessons are the perfect way to have a wonderful adventure underneath the waves in Boston. After your PADI Open Water Diver course, you will get your scuba diving certification. This is one of the most popular scuba courses in the world. Join the millions of other people who have attended the course and you will then be able to dive anywhere in the world, experiencing the best of the aquatic world and its marine inhabitants. The minimum age for the course is 10 years and it takes three days with a maximum depth of 60 ft (18 m). The use of scuba and snorkeling equipment is included in your open water diving course.

Visited this place?

9. Go whale watching aboard a high-speed catamaran

Take a trip on a high-speed catamaran, around the Stellwagen Bank National Marine Sanctuary in Boston, to see the best of the marine wildlife. You are likely to see humpback, right and fin whales along with Atlantic white-sided dolphins on your trip. The whale-watching cruise is narrated by a New England Aquarium Naturalist. Enjoy food and beverages from the on-board galley while enjoying the incredible view.

Visited this place?

Outdoor fun in Boston

Whether your preference is for a hike, a biking experience, or a fun sail on the open sea, Boston has plenty to offer. You can also learn how to play rugby, practice for the Boston Marathon, experience the thrills of whale watching, or try your hand at an exciting scavenger hunt. These are just a few of the best outdoor activities in Boston, Massachusetts.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

History


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Anne Sewell was born in England, but has spent most of her life in Africa - Malawi, Zimbabwe and South Africa - and now resides on the beautiful Costa del Sol in southern Spain. She loves writing...Read more

 Want to contribute as a Local Expert?
Register Here
0 Comments
Explore Boston
Looking for accommodation?
x
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.
hotels with rooftop pool in boston ma

13 Best Hotels With Rooftop Pool In Boston, Massachusetts - Updated 2024