You can’t beat Boston for cycle-friendliness. The area’s flat terrain and preponderance of densely packed communities means that you can cover a lot of ground in an afternoon. Here are some of our favorites:
Minuteman Bikeway: This is about as green and secluded as you can get while still being spitting distance from a bustling spot like Davis Square. Built on an inactive railroad, the 10-mile route grows increasingly woodsier from Cambridge’s Alewife Station into Bedford, and roughly approximates Paul Revere’s famous midnight ride route through Lexington and Arlington
Southwest Corridor Park: What was slated to be an eight-lane highway back in the ’60s has blossomed into a popular commuter trail that zips along Orange Line T stops all the way from Forest Hills to Back Bay. It’s a quick five-mile jaunt, which means diversions are in order, like shooting some hoops or staying cool in one of the route’s spray pools.
Arnold Arboretum: Thinking about postponing that bike ride one more weekend? You might want to reconsider when it comes to the 125-year-old Arboretem, whose future has become increasingly uncertain as it’s developed a nasty infestation of tree-devouring beetles. For a grand finale, ditch your bike and hike up the Peters Hill summit—its views of the Boston skyline are second to none.
The Charles River: The standard, the stand-by, the safety-school of rides, there’s no more obvious choice than cycling alongside a beautiful river that neatly segments the vibrant heart of the metro-Boston area. Reaching from the Watertown Bridge to the Museum of Science, the bigger question is where (and on which side of the Charles) to jump on. One highlight is the Soldiers Field Road section that traverses the Hatch Shell and spills onto a beautiful sunbath-friendly dock next to Longfellow Bridge. Adventurous souls are advised to partake at night rather than during those jam-packed Sunday afternoons when they shut down Memorial Drive.
Charlestown Waterfront Bikepath: There may be other Oceanside routes, but Charlestown is likely the only one that features some badass old-timey warships. This jagged trajectory takes you past the Charlestown Navy Yard and the USS Constitution. Stop for a picnic at City Square Park in Market Square, which looks out onto both the Zakim Bridge and a colorful assortment of over 70 varieties of trees and flowers. The ride’s barely a mile as the crow flies, so some more urban exploring may be necessary—from the storied grounds of Bunker Hill Monument to the ziplines of Barry Playground.
Boston Harbor Walk: This waterfront parkway will eventually encompass 47 miles of smooth pavement, but for now you can get a taste with the South Boston stretch along Old Harbor. Fort Independence Park is filled with moms and strollers, and is open to the public on weekends and Thursday evenings for a pretty breathtaking view of all those skyscrapers downtown. For you budding historians, there’s also the nearby JFK Library and Museum.
East Boston Greenway: Colorful chalk drawings adorn the Greenway, which passes through Bremen Street Park and is a stone’s throw from Santarpio’s Pizza. Belle Isle Marsh is home to swooping ospreys and hawks that you can observe from a watchtower with a weathervane in the shape of a fish. (Why not?) The Blue Line allows bikes on weekends, so you may want to skip over to Government Center and T it to Maverick. Otherwise, take the trek around the Mystic River and through the endearingly bumpy industrial rubble of Chelsea.
Stony Brook Reservation: Haul your mountain bike down to West Roxbury’s 475-acre Stony Brook Reservation, with its dozen miles of bike paths and prime fishing real estate at Turtle Pond. Only got road tires? No matter—you can still soak in a pretty ride cycling along Ennekin Parkway and Hyde Park’s Mother Brook, which is the oldest canal (c. 1639) in the country. Another milestone: the water tower at the top of Bellevue Hill Road, which marks the highest natural point in Boston. Okay, so it’s only 330 feet high, but we said this city was flat, didn’t we?