Explore the City with These Six Bike Trips around Boston

Spontaneous day trips are good for the soul—whether you’re driving a car, on a boat, or pedaling a bike. And never have day trips been more needed than during the time of quarantine and social distancing due to the COVID-19 pandemic. Spending days on end cooped up in your home and staring at the same four walls could drive even the most mentally self-aware Zen master crazy. To help you get out of the house, here are bike trips exploring scenic views across Boston, each complete with a pit stop midway to refuel and reenergize, organized in order of difficulty from beginner to advanced.

Using the Google Maps app on your phone enter each location and toggle to the “bike” transportation mode. Follow the directions, abiding by your own intuition, of course—there are no directions needed for curiosity.

Salem Street in the North End Photo by Tessa Yannone

Boston Common to Monica’s Sub Shop and the Boston Harborwalk

If you’re new to Boston, or just haven’t seen downtown in a hot minute, strap up for this short jaunt through the city—it’s even better now because there are fewer cars on the road and fewer tourists in the street. Begin at the Boston Public Garden, where you can leisurely pedal through the grounds of the park looking at the flowers and trees that come alive during the spring and summertime. Make your way north through Boston Common on Beacon Street, then take a right on Park and a left on Washington Street until you get to the Old State House. When you arrive at Cambridge Street, turn left and then make a right on Sudbury Street.

When you’ve made it to the historic North End, pedal your way up Salem Street and pop into Monica’s Mercato for an Italian sub, and maybe grab a bottle of bubbly or a six-pack of Harpoon. If you have a ravenous sweet tooth, head next door to Bova’s Bakery for a cannoli or three. When you’ve loaded up on enough food to last you a lifetime, take your fare down to the end of Salem and start pedaling to the Harborwalk off of Congress Street. Pick a bench, a rock, or a dock to lay out your feast and dig in. Once the bubbles have settled and you’ve had time to digest the pound of meat you just inhaled, continue down the Harborwalk to the New England Aquarium before jutting off back through downtown and back to the garden. Total roundtrip mileage for this Boston tour is about 4 miles.

Esplanade by Myles Tan via Flickr/Creative Commons

DCR Hatch Shell to Felipe’s Taqueria

Meet your buddies at the DCR Hatch Shell on the Esplanade (a good center point for just about anyone living in the city) and make your way down the Charles River path to Harvard Square. The trip is about four miles one-way, steady and flat, which makes it a great trip to take with tots in tow or newbie bikers. When you get to Harvard Square, you might not be able to enjoy margs and chips and guac on the crowded porch patio of Felipe’s Taqueria, but order ahead and take tacos-to-go or a loaded burrito bowl with a seltzer water to quench your thirst. Take your tacos over to the riverside to enjoy the breeze and watch kayakers paddle by as you chow down. Just be sure to bring a backpack for your leftovers—there’s nothing worse than heavy Mexican food sitting in your stomach while riding a bike. The round trip will top out at 8 miles.

Jamaica Pond by Bev Sykes via Flickr/Creative Commons

The Arnold Arboretum to the Jamaica Plain Pond to El Oriental de Cuba

Undoubtedly the best place to ride bikes in Boston is Jamaica Plain, where the dwellers of this eclectic neighborhood often opt for two wheels instead of four. Plus, you don’t have to venture far out of the neighborhood to get a good adventure in. Be prepared to work on this route, though—the hills in the Arboretum can be tough! With that said, start at the southern tip of the Arnold Arboretum at Peters Hill. Venture your way through the botanical garden gawking at the massive trees and beautiful landscape. Maybe hop off your bike and take a few pictures or take a break under the shade. When you’ve made your way out the other end of the Arboretum through the entrance closest to the Arborway (where the Hunnewell Visitor Center is located), keep pedaling north until you get to the Jamaica Plain pond. Take the outer path, clear from walkers, and make your way around the pond until you get to the other side.

When you make it to the north side of the pond, continue along the path where Perkins Street meets Chestnut Street through Olmstead Park, along Pond Ave., where you’ll reach a bridge right before you get to Washington Street. Turn around here and loop back towards El Oriental de Cuba, a tasty little Cuban spot across the street from the Whole Foods on Centre Street. Grab a Cuban sandwich and a smoothie and camp out on the sidewalk, or make your way back to the pond for a picnic before making the trek to Peter’s Hill. The total distance for this trip spans about 9 miles, but you can opt to just go around the pond for a shorter excursion if the hills have you gassed.

Larz Anderson by Amie Fedora via Flickr/Creative Commons

Larz Anderson Park to the Pump Track and Roxy’s Grilled Cheese

Calling all mountain bikers, skaters, and down-right adrenaline seekers. Start this trip at Larz Anderson Park in Brookline, where there are large sweeping fields and huge hills (touted as the best sledding hills in the city during the winter time) and start pedaling north to Allston via Lee Street, until Lee turns into Walnut Street. When you reach Cypress Street, take a left and then another left onto Harvard Street, where you’ll pass by locally-owned businesses like Brookline Booksmith, the Coolidge Corner Theatre and funky eclectic shops in Allston.

Once you make your way over the Mass Turnpike by way of a small footbridge and into Allston, you’ll head down Franklin Street and find a very cool skate park, built for practicing your mountain bike turns, jumps, and hill turns. It’s called the Vesolutions Pump Track, and it’s like no other skate park you’ve seen before. Just be sure to take turns as you shred the course, and watch out for little kids, who are certainly not watching out for you. After you’ve officially tuckered yourself out on the track, head back the way you came and swing by Roxy’s Grilled Cheese for a classic three cheese sandwich or mushroom burger before pedaling the four miles back to Larz Anderson Park, where lush green fields await for a nap. This route is about 10 miles roundtrip.

Neponset River by Ornoth via Flickr/Creative Commons

Stony Brook Reservation to Neponset River Trail to Yellow Door Taqueria

Reserve this adventure for Saturday or Sunday, as it’s a little bit longer and offers many areas of Boston to explore, including two different wildlife reservations. Begin the journey in Hyde Park at the Stony Brook Reservation, where you’ll find a small urban forest, spray deck, and Turtle Pond. Reserve your energy, though, because you’ll make the six-mile trip from the reservation to the Neponset River Trail, where you’ll go through covered bridges, over the tracks where the Mattapan trolley traverses, and follow the river all the way out to the small inlet to the ocean. Once there, you can either hunker down on the docks with a packed lunch or head back a mile to Yellow Door Taqueria for some of the city’s best tacos. After you’ve fully satisfied your hunger, hop back on your bike and continue the five miles back to Turtle Pond where you can wade knee-deep into the pond, or douse yourself in the Olsen Spray Deck or swimming pool to cool off. This route rounds off at 12 miles, and is best for intermediate bikers, but it’s a good transition route for beginners who want to test their endurance.

Wollaston Beach by Bill Ilot via Flickr/Creative Commons

Savin Hill Park to Wollaston Beach to the Lobster Stop

This trip is for experienced cyclists, as it’s the longest on this list and requires a lot of road cycling. For those up for the challenge, begin the journey at Savin Hill Park, right on the edge of the Dorchester Bay, and across the street from the Malibu Beach dog park. You’ll pedal south, across Morrissey Boulevard, where you can see boats coming in and out of the Dorchester Yacht club. If you made sure to wear your swim suit, make a pit stop at Wollaston Beach in Quincy, where you can take a quick dip or take your shoes off and feel the sand. When you’ve had enough of the sand and saltwater, keep venturing south until you get to the Lobster Stop, located right before you go over the Fore River Bridge—as if you were traveling to Scituate or Weymouth. The parking lot of this local establishment is almost always packed with cars, but that’s just how you know it’s good. Head inside, where you’re greeted with quintessential New England decor and tanks of live lobsters. Grab a lobster roll, or two, wash it down with a water, and hop on your bike back to Savin Hill. This trip totals nearly 17 miles.