Top 5 Boston Bike Rides

by Alex

With its wind tunnels, temperamental weather patterns, and famously cranky drivers, one would be forgiven for thinking that Boston is not a particularly bike-friendly city. While these factors may (or may not) be true, there are plenty of beautiful bike paths in Boston just waiting to be explored. In this post, we’ve mapped out our favorite routes– read on for our top 5 Boston bike rides! 

Grab your helmet, because Boston biking is calling! 

Alex used to bike as his primary mode of commuting to and from work downtown. While that is possible (and many people do commute by bike) neither of us owns our own bikes anymore.

How, you ask? Well, allow us to clue you into a great Boston tip. Boston’s Blue Bikes, a bike rideshare service, offers a variety of options including day passes, single rides, and month- or year-long memberships.

The year-long membership (the most economical option as residents) allows us to take unlimited rides, so long as we stay under 45 minutes for each ride. With a multitude of bike dock options located all around the city, it is easy to find a place to hop on any of these routes from wherever you’re coming from. If your ride is approaching the 45-minute mark, it’s easy to just dock your bike, wait a moment or two, and then hop back on.  

Biking is a great, low-impact activity that anybody can enjoy, and it allows you to see so many parts of our beloved city that are both on and off the beaten path.

Much of Boston is luckily pretty flat, and distances are not too far, which often makes biking the quickest and most direct way to get around. Of course, our disclaimer here is that, like any major metropolitan area, you should exercise a lot of caution while city biking. Pedestrians are known to walk out in the middle of the street at random, and some drivers have the unfortunate habit of using bike lanes as passing lanes to get around other cars.

For that reason, we have tried our darndest to map out bike routes for you that are primarily located on bike paths or bike lanes, making for a more enjoyable and protected ride. For our recommended biking gear, including helmets and bike-friendly packs, see our post here!  

Read on for our Top 5 Boston (and Boston-adjacent) bike rides! Enjoy!

Top 5 Boston Area Bike Rides

 #1: The Emerald Necklace 

The gorgeous set of 6 interconnected parks known as the Emerald Necklace stretches from Brookline to Dorchester. It was named for its location on the neck of the Shawmut Peninsula, before the city had much of the surrounding land filled in the 1800s. These parks were originally designed by famed landscape architect Frederick Law Olmsted, and are truly one of Boston’s greatest treasures.

Each of the 6 are worth exploring: the Fens, the Riverway, and Olmsted Park are all right next to each other, and great to spend a day exploring as a group; Jamaica Pond offers a gorgeous water view as you take a lap around; Franklin Park has a really fun zoo; and the Arnold Arboretum, the oldest public arboretum in North America, has 281 acres of splendor to share. Check out this map for more details! A bike ride around the Emerald Necklace is great for those who want to feel like they’re surrounded by nature while still remaining in the city.

In less than an hour, you can bike from downtown Boston to Jamaica Pond and the Arnold Arboretum.  If you were to follow the Emerald Necklace from its origin in the Boston Common to its end in Franklin Park, you would hit some of the best parks any American city has to offer. This route takes you through the Boston Common, the Public Garden, the Commonwealth Mall, Back Bay Fens, the Riverway, Olmsted Park, Jamaica Pond, the Arnold Arboretum and finally drops you off in Franklin Park. 

We love this area so much– it is so beautiful, and also super practical. We bike or walk on some portion of the Emerald Necklace at least once a week due to its proximity to so many points of interest in the city, as well as to our neighborhood. Whether you are heading downtown or over to JP or Dorchester, the Emerald Necklace is a great resource.

Note: the Emerald Necklace does not have a unified bike path, but you can ride much of it on a paved path.

#2: The Charles River Esplanade

Our favorite bike route in Boston is definitely the Charles River Esplanade. This bike path runs parallel to the magnificent Charles River, and is an ideal way to see the sparkling river and its surrounding nature without worrying about cars.

You can catch the Esplanade at multiple entry points from downtown Boston or from the bridges in Back Bay and beyond. The path itself is paved very nicely, sandwiched between the Charles River and Storrow Drive on the Boston side. The majority of the path is shared with pedestrians, but there are some sections that are designated for bicyclists. 

For those who are using Blue Bikes, there is a perfect spot to pick up or dock your bike right by the Public Garden near Beacon Street: if you cross over Storrow Drive using the Arthur Fiedler Footbridge, you can access the Esplanade right away from there.

From any entrance to the Esplanade, you have several options:

–Turn right, and go for a short ride up to the Boston Museum of Science (near the Lechmere area), where there are great vistas of old Boston Harbor equipment and the iconic Tobin Bridge. There’s a docking station right at the entrance to the Museum if you want to stop in for a visit. For more information about the Museum, see here

–From the museum, you can either make your way back the way you came, via the Boston side of the Esplanade, or you can take your bike over to the other side of the river to the Cambridge side and make a loop from there.
We super recommend doing this, in order to see the Charles River from both sides. To get back to the Boston side, ride back to the BU Bridge, which pops you out on Commonwealth Avenue.
Note: there are some squirrely parts on the Cambridge side where you may have to walk your bike because of narrow sidewalks, but we recommend doing the full loop anyway! 

–Alternatively, you can turn to the left upon entering the Esplanade, and ride all the way out to Watertown. This route is much less transited than the path to the Museum of Science, and is still very well-paved and smooth.
There’s lots of river vistas, little lagoons and gardens, and parks on this side that are absolutely wonderful. Once you go as far as you’d like, you can either turn around and come back the way you came, or cross over on any of the bridges and come back via the Cambridge side.

–It’s easy to utilize the Esplanade to connect with other parts of the city, too, such as biking through the Public Garden or the Boston Common; the Freedom Trail; or the North End areas of Boston. Don’t miss our multitude of Boston guides for what to see in all those areas! 

Along the Esplanade (on both sides) are many spots to sit down and relax before you continue biking. We highly recommend checking out the sunset from one of the docks (pictured above), to take in spectacular views of the skyline, bridges, and other surroundings.

Biking along the Esplanade is especially beautiful in the fall, as you are able to admire the leaves changing colors up close and see the trees up and down the river.
In the spring and summer, the Esplanade is one of Boston’s most popular areas to go out for a stroll or a run.

Its central location and miles of uninterrupted path make this spot ideal as a way to get from one end of the city to the other. 

#3: Fresh Pond + Harvard Area, Cambridge:

Another bike ride we do frequently is biking from our neighborhood (Coolidge Corner in Brookline) to the Harvard University and Fresh Pond Reservoir area in Cambridge. 

You can access the Harvard area from a variety of directions, including the Charles River Esplanade mentioned above! If you’re coming from the Fenway or Brookline area, it’s easiest to bike through Lower Allston and cross the Anderson Memorial Bridge. Prior to crossing the bridge, you’ll see the Harvard Stadium on your left and Harvard Business School on your right. It’s a beautiful detour to bike around HBS for a little bit and check out the classic collegiate atmosphere.

The Anderson Bridge (btw, make sure you stop here for a beautiful view of the river!) turns into JFK Street. If you continue straight it becomes Harvard’s campus. There are lots of protected bike lanes around here that you can use to navigate around the campus and nearby square area. Harvard has upgraded lots of colonial and Victorian buildings into academic and administrative buildings that are lovely, and of course you can’t miss the iconic Harvard Yard.
Note: If you want to dock your bike for a bit to walk around, check out Harvard’s world-class museums, or grab a snack, there are lots of docks nearby. The one near Harvard Kennedy School usually has bikes and docks available.

From Harvard, it’s a very quick ride (less than 10 minutes) to Fresh Pond. Hop on Brattle Street, heading west into West Cambridge. From there, turn right onto Fresh Pond Parkway and you’re practically there! 

Fresh Pond Reservation is a beautiful walking loop– each lap around the lake is 2.25 miles, with plenty of green space, gardens, and shade, as well as a 9-hole golf course. See here for a trail map. Interestingly, the water from the lake (known as a “kettle hole” lake because it formed when glaciers and floodwaters receded) was used back in the day to harvest and ship ice all over North America, and even as far as Asia in its heyday. Nowadays, it’s owned by the city of Cambridge, but is still used as a municipal water source.

After spending some time at Fresh Pond, definitely make sure you check out the Brattle Street area, weaving through the gorgeous neighborhoods and checking out the architecture. There are excellent bike lanes on this wide, boulevard-style road, and it really can’t be beat on beautiful days.

While here, don’t miss the Longfellow House! Home to famed poet Henry Wadsworth Longfellow, it previously served as George Washington’s headquarters during the Siege of Boston in the American Revolution. Also nearby is the Mt. Auburn Cemetery, founded in 1831 as the first “garden-style” cemetery in the U.S. and now a National Historic Landmark and lovely place to walk around.
Note: We usually dock our bikes at the Mt. Auburn Hospital near Ten Ten Memorial Drive if we’re running low on time. 

#4: The Southwest Corridor + Arnold Arboretum:

The Southwest Corridor is a park and bike path stretching from the Back Bay to Forest Hills areas in Boston.

The area was slated to become a 12-lane expressway in the 1970s, but fervent community action prevented this from taking place, and instead was re-designated as a multi-purpose area for public transportation and recreation, with each neighborhood advocating for what they wanted it to look like. It took 9 years to build, but the end project incorporated everything each neighborhood wanted: below-ground trains in the South End, lots of park space for children, and lots of gardens to be maintained by volunteer stewards.

Today, the Southwest Corridor boasts a 4.1 mile (one-way) greenway-style bike path with a variety of parks, playgrounds, and basketball, tennis, and other recreational courts, as well as miles of trails off the bike path.

The bike path itself is very well-paved, smooth, and clearly marked. There is some street biking here, but all in a designated bike lane. We love the Southwest Corridor because a large portion of it is protected bike lanes, a rarity in Boston. For Southwest Corridor maps, see here.

From the Southwest Corridor, you can easily explore some of Boston’s best neighborhoods, such as Roxbury, Jamaica Plain, and the South End. You can also check out Northeastern University‘s campus (as well as the other colleges and universities in the area), the Museum of Fine Arts, and more.
The biking gets a little rocky once you get closer to the terminus in the South End/Back Bay (the lanes could really use re-paving), but you can just dock your bike and continue to explore by foot.
There are tons of places to eat and explore in the South End, especially in the Washington Street area, and it’s easy to walk around Back Bay from there as well. Check out our Back Bay and South End tips in our Boston 101 guide here.

We usually pair biking the Southwest Corridor with a visit to the Arnold Arboretum, the oldest public arboretum in North America. Established in 1872, the Arboretum is now owned and operated by Harvard University, but it largely self-managed and self-funded. It is still an active botanical research institution with a large research presence, but is enjoyed by all as a 281-acre park with interconnecting short trails, small meadows, rose gardens, and places to relax.

You can easily spend a half-day here,
Don’t miss Peters Hill for a fabulous view of the Boston skyline, and the Larz Anderson collection of adorable mini-bonsai trees. We usually dock our Blue Bikes at the Forest Hills MBTA stop and enter the Arboretum through the Bussey Brook Meadow. From there, you can explore all over the park. For an interactive map, see here

#5: The Minuteman Trail:

New England is a region known for its abundance of parks and trails, but we think the Minuteman Bike Trail is one of its most special.

Built on an old train line, the trail is a delightful, paved way to see some of the most famous sites from the American Revolutionary War period by bike. Have you ever wondered what it was like to go on Paul Revere’s Midnight Ride? Riding your bike between Lexington and Concord may not have the same gravitas as a galloping horse, but feel free to yell “The British are coming! The British are coming!” all the same. Despite its length, the 10-mile bike ride flies by due to super-smooth bikeways and an almost-entirely flat terrain.

Biking the Minuteman in whole or in part is a great way to spend a beautiful New England summer day, and is fun for solo bikers, couples, or for the whole family. 

Since it’s a bit further out and more detailed than our other Boston Biking favorites, we decided the Minuteman Trail deserved a standalone post– check it out here!  

Where are your favorite places to explore by bike in your city? Let us know in the comments! 

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