Boston's best: Bike rides
While this city could probably stand to have fewer potholes and more bike lanes, geographically speaking, 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. (Teele Square to Jamaica Pond clocks in at eight miles—or barely as much time as it takes to watch an episode of Jersey Shore.)
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. Pay attention—this trail’s well-tread by bikers, walkers, joggers and in-line skaters alike. We recommend soaking in a sunset at Spy Pond and cycling through Lexington’s Great Meadows wetlands. There’s an extension at the end that sends you to Concord via a national wildlife refuge or two...
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. Stop by Blunch (59 East Springfield Street, South End) for a sandwich and get 10 percent off with a Bicycle Benefits sticker. It’s also worth trekking to the massive and well-manicured Forest Hills Cemetery, with its gorgeous sculptures and famous headstones ( we see y.o.u., e.e. cummings!)
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. Take the Jamaicaway over to JP/Roslindale to revel in its 265 car-less acres of pines, oaks and occasional bonsai gardens. 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.
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.
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. Carson Beach is a great spot for frisbee and volleyball, though we aren’t necessarily chomping at the bit to swim in the water. 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.
Eastie gets a bum rap, but its parks are as picturesque as they are uncrowded. 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.
Looking for a woodsier all-terrain route? 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?