I don't really like trails and paths. I like roads; roads go places. Like from where I live to where I don't live, thus places I want to visit. There are some roads I'm not allowed on like the Tobin Bridge, and the Sumner Tunnel, and well all of the interstate highway system really, but I've found the alternate routes are generally pretty good.

Bestest Rides

  • Farm Pond in Sherborn via Hale Reservation (Dover) back through Wellesley/Newtown details (June 2003)
  • Bikes not Bombs 62 Mile Ride: Jamaica Pond - Farm Pond - Foxborough Stadium - Massapoag Lake - Bikes not Bombs World Headquarters (Fall 2002)
  • Le Tour de Nouv Hampseur Stage 1: "Cities in New Hampshire with the Same Names as Towns in Massachusetts" a.k.a. "Manchester and Concord" (Summer 2001)
  • Le Tour de Nouv Hampseur Stage 2: "The Tri-Stater" a.k.a. "Charles-Piscataqua River Race" details (Summer 2002)
  • Le Tour de Nouv Hampseur Stage 3: "The Boston-Nashua-Salem Triangle" a.k.a. "There and Back Again" (Summer 2002)

Shorties but Goodies

  • Wellesley via Beacon or Comm. Ave. (especially fun with a stop at the Organic Farm)
  • Walden Pond, any which way
  • MIT Cycling's Concord Ave - Trapelo Road Loop
  • Top of the hill at Brandeis
  • Top of the hill at the Arboretum, via Southwest Corridor Park
  • Flax Pond, Lynn (Cape Anne warmup ride) details

Le Tour de Nouv Hampseur Stage 2: "The Tri-Stater" a.k.a. "Charles-Piscataqua River Race"

Boston, MA - Portsmouth, NH / Killery, ME

This was probably the best ride I've had in the US. Its really nice, rather flat and fast, and absolutely beautiful towards the end. The route is pretty straight-forward, wiggle your way through Cambridge, Everett and Revere till you get you to 1A (lots of signage around the Revere Beach area), then just stay on 1A straight through to Portsmouth. To get to Maine, follow the signs for downtown Portsmouth, then take State Street (which is US-1, this is the only time its ok to be on US-1) over and you're there. 1A is pretty welled signed all the way through, but I'll note some tricky spots below. Its somewhere around 60-70 miles one way. There is quite good bus service back to Boston from Portsmouth on C&J Trailways, or Concord. The route looks something like this:

Flax Pond, Lynn (Cape Anne warmup ride)

Boston, MA - Flax Pond, Lynn: 14.1 miles as MapQuest drives, about an hour on the bike, pretty hard pace.

Working out a route to Cape Anne. The first stretch of this made me think it was going to be awful, but its quickly gets very very nice. Here's a quick summary:

Farm Pond, Sherborn

Boston, MA to Farm Pond Sherborn: 16.9 miles as MapQuest drives. ~25 or more via Hale Reservation in Dover, ~20 via Beacon/Route 16

Farm Pond is like Walden, but bigger and better. Large pond with pretty sizeable beach. Lots of families out swimming, also a bit of sailing and other small boating. Loop I did was something like this: