Top 14 Outdoor Activities in Boston | Red Roof

Top 14 Outdoor Activities in Boston

Charles River with Boston skyline

Looking for some fresh air and outdoor fun? Red Roof has compiled a list of the best outdoor activities in Boston. From scenic parks to exhilarating hiking trails, there’s something for everyone to enjoy. Plus, our affordable hotels are conveniently located near these outdoor gems, making it easy to get out and explore!


Boston is a city renowned for its rich history, beautiful architecture, and bustling city life. But what many people don't know is that the city also has a plethora of things to do outdoors in Boston for those who are looking to escape the hustle and bustle of the city.


From hiking trails to parks, there is something for everyone in this vibrant city. In this guide, we will take you through some of the top outdoor activities in Boston so you can make the most of your visit to this amazing city.

Two people kayaking

Kayaking on the Charles River

The Charles River is a beautiful waterway that runs right through the heart of Boston. It offers stunning views of the city and is the perfect place for kayaking. There are several rental companies along the river where you can rent a kayak or even take a guided tour. The most commonly used of these are at Kendall Square and Christian A. Herter Park, where you can rent single or double kayaks and even paddleboards.


This is a great way to explore the city from a different perspective while getting some exercise at the same time. The views of the city skyline and famous landmarks such as the Zakim Bridge are simply breathtaking from the water.

Boston skyline viewed from a forested hilltop

Hiking at Blue Hills Reservation

Located just south of Boston, Blue Hills Reservation is a scenic park with over 125 miles of trails for hiking, biking, and horseback riding. The trails vary in difficulty and length, catering to both beginners and experienced hikers alike. The park also offers stunning views of the Boston skyline and surrounding areas.


For those seeking a challenge, hike up to the summit of Great Blue Hill, the highest point in the reservation. From here, you can enjoy panoramic views of Boston and beyond. The park is easily accessible by public transport, making it a convenient option for visitors without a car.

Boston Common path at sunrise

Biking on the Emerald Necklace

The Emerald Necklace is a series of parks and green spaces that connect some of Boston's most iconic landmarks. This 1,100-acre park system offers plenty of opportunities for outdoor activities, including biking.


Rent a bike and explore the beautiful trails that wind through parks such as the historic Boston Common, Public Garden, and Arnold Arboretum. You can also join a guided bike tour to learn more about the history and architecture of these parks.

Picnic with wine and fruit

Picnicking on Boston Common

Known as America's oldest public park, Boston Common is a must-visit for any outdoor lover. This historic park offers plenty of green space for picnicking, walking, and people-watching. The picturesque Frog Pond also offers seasonal activities such as ice skating in the winter and a spray pool in the summer.


For those looking for more outdoor activities, there are also various sports courts and fields throughout the park. And don't forget to visit the iconic George Washington statue, located at the heart of Boston Common.

Person swimming in clear water

Swimming at Spectacle Island

Located just a short ferry ride from downtown Boston, Spectacle Island is a hidden gem for beach lovers. This serene island offers a beautiful sandy beach and crystal-clear waters, perfect for swimming and sunbathing.


The name Spectacle Island comes from its unique shape, resembling a pair of spectacles when viewed from above. In addition to swimming, the island also offers hiking trails and stunning views of Boston's skyline.


The island also has hiking trails that lead to amazing views of Boston Harbor. Visitors can learn about the history of the island at the Visitor Center, which offers interactive exhibits and guided tours.

Sandy beach and calm sea

Head Down to the Beach

When you think of Boston, the first thing that comes to mind may not be beaches. But Boston is actually home to several beautiful beaches where you can spend a relaxing day by the ocean.


Some popular options include Revere Beach, Carson Beach, and Castle Island. These beaches offer sandy shores, calm waters for swimming, and stunning views of the city skyline. And if you're feeling hungry after some fun in the sun, there are plenty of seafood restaurants nearby to grab a bite.

Boston skyline at sunset

Take a Harbour Cruise at Sunset

For a more relaxed outdoor activity, why not take a harbor cruise at sunset? Several companies offer cruises departing from Boston's Long Wharf. You can enjoy the cool ocean breeze and watch as the cityscape transforms into a golden glow during sunset.


Some cruises even offer dinner or drinks on board, making it the perfect romantic evening or a fun night out with friends. And if you're lucky, you may even spot some dolphins or whales during your cruise.


The views of Boston from the harbor are simply unmatched, making this a must-do activity for any visitor to the city.

Massachusetts State House with golden dome

Walk the Freedom Trail

The Freedom Trail is a 2.5-mile walking trail that takes you through some of Boston's most significant historical landmarks. As you walk through the city, you'll learn about the rich history and culture of Boston and its role in shaping America.


The trail begins at Boston Common and ends at Bunker Hill Monument, passing by 16 historic sites along the way. These include:

  • The Massachusetts State House - Built in 1798, this iconic building is still the seat of state government.
  • The Old State House - This was the site of the Boston Massacre in 1770 and now serves as a museum.
  • Paul Revere's House - The home of the famous patriot and his family from 1770 to 1800.
  • Faneuil Hall - A popular marketplace and meeting hall, also known as the "Cradle of Liberty."
  • USS Constitution - The oldest commissioned warship in the world, also known as "Old Ironsides."


The Freedom Trail offers a great way to spend a day outdoors while learning about Boston's fascinating past. Guided tours are available, but you can also walk the trail on your own with the help of a map or smartphone app.


The red brick path is easy to follow and takes you through some of Boston's most charming streets, making it a great way to explore the city on foot. Plus, many of the sites along the trail offer free entry, making it a budget-friendly activity.

Painted rock

Check Out The Art Quincy Quarries

For a unique outdoor experience, head to Quincy Quarries Reservation. This former granite quarry is now a popular spot for rock climbers and hikers, offering stunning views of the Boston skyline.


Originally used as the source for the granite used in many famous buildings, such as the Bunker Hill Monument and the U.S. Capitol building, Quincy Quarries is now a public park with easy hiking trails and rock climbing routes for all levels.


But what makes this park truly special is its collection of colorful graffiti art on the rock walls. The art changes frequently, making it a must-see for any street art enthusiast. It's also a great place to take some Instagram-worthy photos.


The park has designated hiking trails, but you can also explore on your own and get up close to the abandoned quarry walls. Just make sure to wear appropriate footwear, as the rocks can be slippery.

Peaceful pond surrounded by greenery

Visit The Arnold Arboretum

Located in Jamaica Plain, the Arnold Arboretum is a 281-acre botanical garden and tree research center. The park is home to over 15,000 varieties of plants from all around the world, making it a must-visit for any nature lover.


The arboretum has paved walking paths and hiking trails that wind through gardens, woodlands, and ponds. You can also join a guided tour or explore on your own with the help of an interactive map.


The park also offers various events and activities throughout the year, such as guided bird-watching walks and educational workshops. And with free admission, it's a great budget-friendly option for outdoor fun in Boston.

Tree trunks

Hike in the Middlesex Fells

Located just outside of Boston, Middlesex Fells Reservation is a nature lover's paradise. The park boasts over 2,500 acres of woodlands, meadows, and ponds, making it the perfect spot for hiking, bird-watching, and picnicking.


There are various trails to choose from depending on your skill level and desired distance. The Skyline Trail offers stunning views of the Boston skyline, while the Rock Circuit Trail takes you past beautiful rock formations and through lush forests.


The park also has a designated area for mountain biking and horseback riding. And with plenty of picnic areas and grills available, it's a great place to spend a sunny day with friends or family.


If you're heading there in winter, remember to bring shoes with good grip, as the trails can get slippery. And don't forget to pack a camera - you never know what wildlife you may encounter on your hike.

Humpback whale breaching from the ocean

Go Whale Watching

For a truly unforgettable outdoor experience, why not go whale watching off the coast of Boston? Several tour companies offer trips from April to October, giving you the chance to see humpback, finback, and minke whales in their natural habitat.


The tours depart from Long Wharf and last for about 3-4 hours. You'll get up close and personal with these magnificent creatures, as they come right up to the boat. You may even hear them communicating with each other through their songs.


Aside from whales, you may also spot dolphins, seals, and various species of seabirds during your trip. And if you're lucky enough to witness a humpback whale breaching - where it jumps out of the water and lands back with a splash - you'll understand why this activity is so popular in Boston.

Waterfront path with benches and historic fort

Visit Castle Island

As you might expect, Castle Island is a small island with an old fort on it. The beautiful scenery and walking paths make it a popular spot for locals and tourists alike.


Located just south of downtown Boston, the island offers stunning views of the city skyline and Boston Harbor. You can take a leisurely stroll along the shoreline or explore Fort Independence, a historic fort built in 1634.


The island also has a beach, making it a great spot for sunbathing and swimming in the summer. You can also grab some seafood at Sullivan's on Castle Island, a popular eatery that has been serving delicious fried clams since 1951.

Woman holding shopping bags

Indulge in Some Retail Therapy at Assembly Row

If you need a break from all the walking, head to Assembly Row in Somerville. This outdoor shopping and dining destination offers over 50 outlet stores, including popular brands like Nike, Levi's, and J.Crew.


But what makes Assembly Row truly unique is its outdoor spaces. The park-like setting features walking paths, water fountains, and green spaces where you can relax and take in the scenery. You'll also find various dining options here, from quick-service restaurants to upscale eateries.


And if you're visiting during the summer, be sure to check out the outdoor movie series and free fitness classes held at Assembly Row. It's a great way to combine shopping with outdoor fun in Boston.


Traveling to Boston? Book a room at one of our affordable, pet-friendly hotels.