The Perfect Cycling Guide to Boston, MA

Boston has become more bike-friendly over the years
Boston has become more bike-friendly over the years | © Global Jet / Flickr
Harry Gustafson

Boston is becoming more and more friendly to bikers. In recent years, the city has added bike lanes to the sides of streets in an attempt to improve the safety of its cycling community.

Loved by over 40s

Becoming more bike-friendly has also made Boston a leader in environmental sustainability. While these cycling lanes make urban biking safer and more fun, there are also plenty of parks and reservations in the area that also provide excellent bike paths and great exercise for anyone using them. Make sure to plan ahead and map your route, especially if you’re going somewhere you’ve never been before!

Millennium Park


Located on the outskirts farthest from Boston in West Roxbury, this large suburban park is used for all manner of recreational activities. With over six miles (9.6 kilometers) of trails, it is a great location for cyclists of all skill levels. Because the park started as a landfill developed on wetlands, it is home to a large population of wildlife. At the highest points in the park, you’ll be able to catch a beautiful view of downtown Boston.

Fresh Pond Reservation


Fresh Pond Reservation boston cycling
© Doc Searls / Flickr

This 2.5-mile (four-kilometer) loop in West Cambridge offers a quick and easy workout. It’s accessible to West and North Cambridge via Alewife, and even from the Harvard area, if you’re willing to tack on a few miles to your trip. The scenic area surrounds a reservoir and includes trails through wooded areas and alongside a golf course. For some extra distance, combine the Fresh Pond Loop with a ride through nearby Danehy Park, which is just up the street.

Minuteman Commuter Bikeway


This 10-mile (16-kilometer) bike path starts near Alewife Station in North Cambridge and travels north all the way to the suburban town of Bedford. The historic route is a rough estimate of the path traveled by the first American militiamen from the Revolutionary War. During the first battles of that war, the Minutemen—a nickname for early American soldiers—pushed their British opponents from Concord, MA, back south to Boston. This route also connects with four other nearby bike paths.

Blue Hills Reservation


blue hills reservation boston cycling
© Bob P.B. / Flickr

Located 10 miles (16 kilometers) south of Boston, this reservation is in the cities of Quincy, Milton, Randolph, and a few others. It is the largest section of undeveloped land in the Boston area. With a bounty of mountain trails, it offers a great challenge for bikers seeking an adventurous woodland ride. With several possible trail combinations—over 40 miles (64.3 kilometers) total—it can provide an intense challenge for experienced mountain bikers.

Southwest Corridor Park


What started as an unpopular project in the 1960s to route Interstate 95 through the Jamaica Plain neighborhood eventually became this linear park that makes its way up to the edge of Boston’s South End. It totals nearly five miles (eight kilometers) in length. The Southwest Corridor is perfect for urban bikers seeking a convenient workout and can even double as a safe shortcut to work for those who live near it. This route intersects with the city’s Emerald Necklace series of parks at the Arborway in Jamaica Plain.

Franklin Park


franklin park boston cycling
© Sarah Nichols / Flickr
Franklin Park lies at the intersection of the neighborhoods of Dorchester, Roxbury, and Jamaica Plain. Its main path covers a little over two miles (3.2 kilometers), filled with peaceful woody areas. The Franklin Park Zoo is also located here. A bike ride through the park and a trip to the zoo can make for a perfect day. You can even pass the ruins of the zoo’s old bear cages.

Stony Brook Reservation


This reservation in Hyde Park contains several trails within its wooded areas, covering anywhere between two and six miles (3.2–9.6 kilometers). It offers a peaceful stretch of nature within an urban area. Stony Brook is an ideal spot for a family bike ride, especially in the spring when the surrounding natural areas are in full bloom. All of the paths are relatively flat and very easy to navigate.

culture trip left arrow
 culture trip brand logo

Volcanic Iceland Epic Trip

meet our Local Insider


women sitting on iceberg


2 years.


It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.


I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!

culture trip logo letter c
group posing for picture on iceberg
group posing for picture on iceberg

Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.

map of volcanic iceland trip destination points
culture trip brand logo
culture trip right arrow
landscape with balloons floating in the air


Connect with like-minded people on our premium trips curated by local insiders and with care for the world

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.