Bicycling in Dorchester/South Boston

Bicycling in Dorchester/South Boston:

The first thing to do is to ride the coastal route. Start in South Boston at Castle Island (where the fort is at the tip of South Boston), and ride along the coast, into Dorchester, around UMass and the Kennedy Library. The route ends at Morrissey Blvd., where you take a left and go over a bridge over a waterway, then under the Expressway.

Here it gets tricky. At the traffic light just after the Expressway bridge, go left onto Freeport Street. Follow that past an auto dealership (a short side trip here would be to go left on Victory Rd., under the expressway and there’s a park on the right just before the Old Colony Yacht Club and Dorchester Gas Tank. The park, called the Troy Landfill Site, was the source of a major scandal in the 1970s that resulted in the disbarment of the chief judge of the Dorchester Court – Judge Jerome Troy), the Phillips Old Colony Restaurant, Candy Shop, bowling alley (you’ll be on a side street right next to Morrissey Blvd.), and at the bowling alley, stay just to the right of the building.
At the stop sign, make a left onto Conley St. (probably no street sign there), and under the expressway. You’ll pass Tenean Beach on the left. At the end of this beach, make the first left onto Lawley St., which takes you into the neighborhood of Port Norfolk, an old industrial area that used to be famous for making nails and boats (there is still a boat place there) and ice cream. Make a right on Ericsson St.,, a right on Walnut St., then a left on Water St. and follow it to the end.
At the end of Water St. , you’ll pick up the Neponset River Bike Trail (there’s a sign), which will take you by a sunken barge, then under the Neponset River Bridge that goes to Quincy). Head south from there, and just follow the path. You can ride through John Paul II Park if you want to see more of the Neponset River, or just keep on the main path, but ultimately you’ll need to go through a tunnel under the Expressway and keep going south along the path. This well-marked path will take you in back of an elderly housing development that used to be a camera factory, then through a new park built where a toxic waste company was located, across Granite Ave. (be careful of cars here), then onto a stone dust path along the river, along a trolley car line to Lower Mills.
The bike path crosses the Neponset River into Milton and then ends at Central Avenue in Milton (it's slated to go all the way to Mattapan Square in the next few years). Cross over the Neponset back into Dorchester, ride up Central Avenue to River Street, and take a right on River St. At the next major intersection (Washington St.) stay right and go to Dorchester Avenue, which is the Lower Mills Business District (there's a good coffee shop called Flatblack and also a nice icecream place called the Icecreamsmith at the intersection of Washington St. and Dorchester Ave, and a funky restaurant called Common Ground just north on Dorchester Ave. at the intersection of Richmond St.)
Back at the intersection of Washington and Dorchester Ave, cross over Dorchester Avenue onto Adams Street (Washington Street turns into Adams St.), and just follow Adams to Gallivan Boulevard. Go right onto Gallivan Blvd to the next big intersection, and go left onto Adams Street (yes it's the same Adams Street, but it goes on hiatus for a quarter mile). That takes you through Adams Village. You'll go up a hill (on right is Oakton St. which has the 2nd oldest house in Boston on it (the Pierce House).
Follow Adams Street, take a left on Ashmont Street. At Dorchester Ave., you’re at Ashmont T Station (you can take a bicycle on the T on weekends and off hours (see the MBTA website for more information). There’s a nice restaurant at this intersection (Ashmont Grill). Continue on Ashmont St., going the wrong way (it turns into a one way heading toward you, you may need to walk) for 2 blocks to Ocean St. Go right on Ocean, and you’ll see a lovely Victorian era neighborhood called Ashmont Hill. Go left on Welles Ave., then right on Washington Street into Codman Square. You can take a pit stop at the health center if you need one.
Continue on Washington St. to the Court House, make a right on Melville Ave., another lovely Victorian era neighborhood), a left on Wellesley Park, Right on Park St., and you come to Fields Corner (the center of the Vietnamese Community). Go left on Dorchester Ave. (Viet coffee shop called Dippin’ Donuts on Dorchester Ave. about midway through the business district), then go left on Adams St., and up the hill to Meeting House Hill. Bear right at the top to pass in front of the 1st Parish Church, a Unitarian Church organized in 1630. Make a right after the church on Church St., then a left on High St. and go down the hill.
At the bottom of the hill go left onto Hancock St., and you’ll come to Uphams Corner, a large Hispanic/Cape Verdean business district. Go right onto Columbia Road, pass the Strand Theater (one of the largest theaters in New England, owned by the City for community purposes), then go right just before the traffic light on Cushing or Mt. Cushing Ave. Go right onto Cushing (2^nd right, just after a church), and up the hill. You’ll pass some splendid Victorian era houses in this neighborhood, called Jones Hill. At the end of Cushing, go left then a quick right down the hill to a traffic light.
Go straight onto Savin Hill Ave., past a Rite Aid Pharmacy, past the Savin Hill T stop, and over the Expressway. Make the second right after the expressway onto Playstead Road, which will take you to Savin Hill Beach. There is a pretty walkway along the beach and playground and yacht club beyond the parking lot if you want to stop. Take the other street out of the parking lot (Denny St.) back to Savin Hill Ave. and go right, you’ll immediately come to a fork, and stay right on Savin Hill Ave. where you’ll pass some lovely Victorian houses, some of which have yards that go to the beach. It curves to the left and you’ll come to a stop sign. Go left and then a quick right onto Grampian Way, so that the park is on your left. You’ll pass an overlook of the city, then take the first right onto Rockmere Street. At the end there’s an entrance to the park. The park is definitely worth seeing, as there’s a spectacular view of the harbor. After the park, go right on Caspian Way down a steep hill, right on Savin Hill Ave., back over the expressway bridge, and back to the corner of Savin Hill Ave. and Pleasant St.
Go right onto Pleasant Street, which curves to the right then to the left at the end onto Pond St., where at the intersection of Columbia Rd. you'll see the oldest house in Boston (the Blake House) in a park on your left as Pleasant hits Columbia Rd. There’s also a statue of Edward Everett, the great 19^th Century politician and orator. Go left onto Columbia Rd to the intersection (Edward Everett Square, where you’ll see a gigantic bronze pear, which honors the Clapp Pear, developed by a local family). Make a right onto Boston St. Go down Boston St. (you’ll pass two old houses on the left – the Lemuel Clapp House (1765) and the William Clapp House (1815) owned by the Dorchester Historical Society, which are open on Saturdays from 2-4, and a nice restaurant called 224 Boston St.) to Andrew Square in South Boston, go right onto Dorchester Street (a slight right) go up the hill and continue to Broadway. Go right onto East Broadway and follow back to Castle Island. It's probably a 20 mile loop, and will give you a good sense of parts of Dorchester and South Boston.
For other routes around the city, contact Hub on Wheels at City Hall. Steve Gag is a great resource 617-635-2338.