Best Outdoor Activities in Boston

Boston's Four Season Activities Bring You Outdoors Throughout the Year

Boston's distinct seasons bring exciting outdoor adventures for year round fun. Visitors of every age can find a way to spend the day enjoying the weather during the winter, spring, summer and fall.

Winter weather may bring dips in temperatures and snow covered sidewalks, but it also brings the opportunity to enjoy ice skating, sledding, and even skiing in and around the city.  Take advantage of the Boston Common where the Frog Pond welcomes you to swirl and twirl around the ice. Or head to the Blue Hills where you can take a hike anytime of year, or even ski at this just outside the city spot. 

When the snow starts to melt and temperatures begin to rise, you'll find the city landscape coming to life. Locals flock to outdoor spaces to enjoy the beauty of the newly verdant landscape dotted with bright blooms. Favorite spots include the Arnold Arboretum, and the Boston Public Garden.

Once summer is in full swing, Bostonians take advantage of the Harbor, and Charles River and make their way to the water. Frolic along the shore or get out on the water by renting a canoe or kayak to tour along the Charles River.  Take a cruise to one of the Boston Harbor Islands, or hang at the beach at Castle Island Park


Hubway is a bike share service with various locations throughout the city. An excellent way to get exercise, and see Boston's best sites, Hubway's bike rental stations are splattered throughout the city for easy use. Discounted rides can b found for regular riders who will benefit from a membership. Options range from a single day membership, 3 day membership or full-year membership. Those seeking to hold on the bike for the entire day beware: costs rapidly increase once you reach the 30 minute ride mark. However, as long as you check your bike into any Hubway location every half hour, you keep your costs down. A little prep work in needed to ensure that your use of Hubway will be an economical alternative to the MBTA, taxi or parking costs.

Recommended for Outdoor Activities because: Hubway is an activity and mode of transportation; use the bikes to get from place to place and return when you arrive at your destination.

Jessica's expert tip: Boston's bike share is a bit ahead of the bike lanes; riders should feel comfortable riding on busy city streets.

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Belkin Lookout Farm offers family fun for everyone! From fruit picking, to farm animals, you'll find a full day of excitement at Belkin Lookout Farm. Pay one price to enter and another to pick then hop on and off their train as you make your way through the gorgeous fruit-filled orchards to the children's play area. Have fun as you climb the playground structures, make your way to the top of the hay pyramid, get your face painted, take a hayride, or bounce away in their bounce house. Pack a lunch and picnic on the grounds, made even better after fruit picking when you can sample the fruits of your labor. Then check out the burlap maze and visit with the animals before heading back to the entrance where their farm stand is packed with delectable items to purchase when you head home.

Recommended for Outdoor Activities because: Belkin Lookout Farm is ideal for families; a train ride, play space, & fruit picking are available into the fall.

Jessica's expert tip: Belkin gets very busy on fall weekends; visit on a weekday and avoid the crowds.

Read more about Belkin Family Lookout Farm →

Boston Public Garden

Take a leisurely stroll through the oldest botanical garden in the United States and get a feel for Boston's charm and grace. 1877 marks the start of the Garden's fame for the Swan Boats that float along the pond when the weather warms; a necessary ride for the kid in all of us. The Swan Boats do not get all the attention, as the grounds truly are a sight to hold. Pack a picnic and sprawl across the lawn to enjoy the beauty of this inner city treasure. Year round, the beauty of Public Garden shines, and makes for excellent photo opportunities.

Recommended for Outdoor Activities because: The Boston Public Garden is beautiful, but a ride on the Swan Boats is a must at least once.

Jessica's expert tip: Ideally located in the heart of Boston so that you can integrate a visit to the Public Garden with other sightseeing in the same day (the Boston Common perhaps).

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Arnold Arboretum

Developed by James Arnold, who left it to Harvard University upon his death. Today, the 281-acre grounds are home to over 4000 types of trees, maintained by Harvard's School of Botany. A botanical garden for students to learn and city dwellers to enjoy is the combination that makes The Arboretum so special. Host to many special events like the ever popular Lilac Sunday each May, scheduled guided walks, tours, and even talks, the Arboretum is, most of all, a showplace for botanical splendor. Be sure to stop into the visitors center where you'll find more information, maps, postcards for purchasing, and activities to engage and teach children.

Recommended for Outdoor Activities because: The Arnold Arboretum lets you wander the hilly landscape learning about botany and enjoying their scheduled events.

Jessica's expert tip: Dining is not offered or permitted on the Arboretum grounds.

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Castle Island Park
Photo courtesy of Castle Island Park

Castle Island is a twenty two acre urban park located along the waterfront and home to Fort Independence. With many paths for walking, biking or running as well as a playground and beaches, Castle Island allows visitors to see a Boston attraction and relax on one of their urban beaches that draw crowds of locals during the summer. With a clam shack on site (Sullivan's) you can stay through lunch and enjoy all that castle Island has to offer including the excellent view of Logan making it the perfect place for plane lovers to watch both take offs and landing.

Recommended for Outdoor Activities because: Castle Island offers visitors the chance to explore its history or simply spend time at the beach moments from Boston's downtown.

Jessica's expert tip: Free and open year round, Castle Island gets crowded during summer months, and parking get difficult.

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Boston's only 3-hour Whale Watch departs from the Harbor for a 3 hour tour on super fast, super comfortable catamarans. Cutting down on time getting to the whales and allowing you more time to check them out. With 3 exterior viewing decks, there is plenty of room to gawk at the giant ocean life below. For those looking to take a break from the elements, the cabins are climate controlled, have ample seating, and snacks for sale. A good place to linger en-route to the whales. Tours are narrated by actual researchers from the Whale Center of New England, ensuring you get the best information out there.

Recommended for Outdoor Activities because: Boston Harbor Cruises- Whale Watching quickly takes you to whale feeding grounds and optimizes your time sighting whales.

Jessica's expert tip: Boston Harbor Cruises- Whale Watching guarantees that you see a whale or gives you a ticket to return again at no cost.

Read more about Boston Harbor Cruises - Whale Watching →

The Boston Common Frog Pond is a four season beauty in the heart of the Common. A wading pool in the summer and ice rink in the winter, the Frog Pond allows outdoor activity in the middle of Boston. Skate around with someone special or teach your kids a few tricks on the ice when the weather lets the water freeze. Open from mid November each year for public skating, this affordable attraction sees its share of proposals each season. When the weather takes a turn for warm, locals make their way to cool off in the shallow waters and fountains providing a free escape from the heat.

Recommended for Outdoor Activities because: The Boston Common Frog Pond operates seasonally allowing ice skating in the winter and wading during the warmer months.

Jessica's expert tip: Check out what's going on each day at the Frog Pond before visiting as it occasionally plays host to special events.

Read more about Boston Common Frog Pond →

Blue Hills Reservation
Photo courtesy of iStock / Vivvi Smak

Minutes outside of downtown Boston, is the Blue Hills Reservation. Here nature enthusiasts can hike, bike, ski, swim, and even enjoy a zoo experience at the Trailside Museum. Spanning over 7,000 acres along Boston's closest suburbs, this is a true green oasis for city dwellers. Plan to spend a day exploring this area because you'll want to wander for hours. Kids get a kick out of the animals at the museum and winter skiing is offered for those who want to take a few runs without going far from the city. Great Blue Hill peaks at 635 feet, the highest of the 22 hills in the Blue Hills chain. This summit provides visitors with a view of the entire metropolitan area.

Recommended for Outdoor Activities because: Hike, or even ski at the Bill Hills Reservation just a few miles outside Boston's city limits.

Jessica's expert tip: Enjoy the Blue hills year-round, not just for hiking or swimming, this reservation offers winter skiing as well.

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With five rental locations you can easily rent a canoe or kayak and set out on the Charles River for the day. Lessons are available for those looking to learn the ins and outs of canoeing or kayaking, but for those just looking for a little recreation on the river, rentals will do just fine. Set out from the banks of the Charles and make your way in either direction to take in the view of Boston and Cambridge from this famous waterway. A leisurely way to spend the day while getting a bit of exercise, Charles River Canoe an Kayak offers group tours and even takes you off the Charles. Rentals and tours on Boston Harbor are are also available. Families are encourages to enjoy with children, and those aged 8 and up can even operate their own kayak.

Recommended for Outdoor Activities because: Amazing views of the city skyline await when you get onto the water with Charles River Canoe and Kayak.

Jessica's expert tip: Guided tours are great for those unfamiliar with the area as you'll get insight along with great sightseeing.

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The Boston Harbor Islands are unique part of the National Park system. 12 ready to explore islands offer a variety of activities for an active island adventure like checking out historic sites, spotting wildlife, taking a hike, getting in the water on a kayak or for a swim, sharing a picnic, doing some fishing and even camping. The islands can easily be explored on your own, but to enhance your visit you may want to partake in one the programs or tours offered on each. A short boat ride is all it takes to spend your day off the coast of Boston having your own island adventure.

Recommended for Outdoor Activities because: The Boston Harbor Islands offer different activities on each island, leaving you many options for exploration.

Jessica's expert tip: Each of the Boston Harbor Islands has something different to offer; check what each has before choosing your adventure.

Read more about Boston Harbor Islands National Recreation Area →


Meet Jessica Polizzotti

Born and raised in Boston, Jessica knows her city like the back of her hand.  Always looking to uncover something new, Jessica keeps up on the latest and greatest Boston offerings. 

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