Best Road Biking in Massachusetts

This list represents the most popular road biking in Massachusetts. Use this list to plan your next Massachusetts road biking trip. Select a state and/or activity below to find even more top trails.

  • #1 Minuteman Bikeway

    5 Reviews

    Arlington, MA

    The Minuteman Bikeway has it all. It’s close to Boston, it’s historic, it’s located in a lush and beautiful area, and it’s great for families. Its historical significance is of particular note. ...
    •  11 miles
    •  Guide

    The Minuteman Bikeway has it all. It’s close to Boston, it’s historic, it’s located in a lush and beautiful area, and it’s ...

  • #2 Cape Cod Rail Trail

    12 Reviews

    Nickerson State Park, MA

    Cape Cod Rail Trail is a hiking and biking trail in Barnstable County, Massachusetts. It is within Cape Cod Rail Trail and Nickerson State Park. It is 16.6 miles long and begins at 113 feet altitude. ...
    •  16.6 miles

    Cape Cod Rail Trail is a hiking and biking trail in Barnstable County, Massachusetts. It is within Cape Cod Rail Trail and ...

  • #3 Cape Ann Cruise

    3 Reviews

    Gloucester, MA

    This ride explores Boston's North Shore. The shorter 22-mile loop circles the rocky shores of Cape Ann, where fishermen's cottages and grand summer homes now share the ocean views. The route ...
    •  36.4 miles
    •  Guide

    This ride explores Boston's North Shore. The shorter 22-mile loop circles the rocky shores of Cape Ann, where fishermen's ...

  • #4 Belmont to Walden Pond Cruise

    2 Reviews

    Belmont, MA

    John Allis, a three-time Olympian, mapped this route in 1972 by tracing the least busy roads leading west from Cambridge. You'll explore the near-rural suburbs of Lincoln, Sudbury, and Weston. ...
    •  33 miles
    •  Guide

    John Allis, a three-time Olympian, mapped this route in 1972 by tracing the least busy roads leading west from Cambridge. ...

  • #5 Falmouth Shining Sea Path

    2 Reviews

    Falmouth, MA

    Enjoy the brilliant views of the Nantucket and Vineyard Sounds on this short trail connecting Falmouth and Woods Hole. Surface: Asphalt. Location: Barnstable County.
    •  4 miles
    •  Guide

    Enjoy the brilliant views of the Nantucket and Vineyard Sounds on this short trail connecting Falmouth and Woods Hole. Surface: ...

  • #6 South Shore-Wompatuck State Park Ramble

    2 Reviews

    Hull, MA

    This ride begins at a popular swimming beach near Boston, next to a musical amusement ride, an antique carousel. Then it explores four of the oldest and most scenic towns gracing the Atlantic ...
    •  26.6 miles
    •  Guide

    This ride begins at a popular swimming beach near Boston, next to a musical amusement ride, an antique carousel. Then it ...

  • #7 Roundabout Rutland Cruise

    2 Reviews

    Paxton, MA

    Even though Rutland lies in the exact geographical center of Massachusetts, still no one knows about it. Which is precisely its appeal to cyclists. Mount Wachusett is a few miles northeast of ...
    •  38 miles
    •  Guide

    Even though Rutland lies in the exact geographical center of Massachusetts, still no one knows about it. Which is precisely ...

  • #8 Cranberry Country Cruise

    2 Reviews

    Plymouth, MA

    This ride begins in historic Plymouth. Before exploring this town, though, the tour heads inland on sandy-shouldered roads for a rolling, 7-mile cruise through the largest state forest in eastern ...
    •  47 miles
    •  Guide

    This ride begins in historic Plymouth. Before exploring this town, though, the tour heads inland on sandy-shouldered roads ...

  • #9 Cape in a Day (or Two) Classic

    2 Reviews

    Boston, MA

    Many cyclists in New England dream about riding from Boston to Cape Cod—it’s a fantasy trip, one they plan to do someday. For others, this tour is an annual event—thanks largely to the American ...
    •  115 miles
    •  Guide

    Many cyclists in New England dream about riding from Boston to Cape Cod—it’s a fantasy trip, one they plan to do someday. ...

  • #10 Lincoln to Great Brook Farm Ramble

    1 Reviews

    Lincoln, MA

    Lincoln, near downtown Boston, is ideal for rides extending through a landscape of woods and fields, country cottages, and grand estates. Walden Pond, the Old North Bridge Historical Site and ...
    •  30.2 miles
    •  Guide

    Lincoln, near downtown Boston, is ideal for rides extending through a landscape of woods and fields, country cottages, and ...

  • #11 Mount Greylock Classic

    2 Reviews

    Williamstown, MA

    In the Northwestern corner of Massachusetts, 3,500-foot-high Mount Greylock rises over North Adams and Williamstown. It is a rarity among New England Mountains in that a paved road crosses its ...
    •  37.2 miles
    •  Guide

    In the Northwestern corner of Massachusetts, 3,500-foot-high Mount Greylock rises over North Adams and Williamstown. It is ...

  • #12 Marblehead Rail-Trail

    0 Reviews

    Marblehead, MA

    Marblehead is one of the nicest beach communities north of Boston. This trail forks in two directions. Both branches are pretty, and both eventually lead to the Atlantic Ocean. The charm of ...
    •  5 miles
    •  Guide

    Marblehead is one of the nicest beach communities north of Boston. This trail forks in two directions. Both branches are ...

  • #13 Hopkinton Cruise

    0 Reviews

    Hopkinton, MA

    This ride begins at the town green in Hopkinton, at the starting line for the world-famous Boston Marathon. Instead of following the busy streets the marathon takes, this ride heads south and ...
    •  41.2 miles
    •  Guide

    This ride begins at the town green in Hopkinton, at the starting line for the world-famous Boston Marathon. Instead of following ...

  • #14 Norwottuck Rail Trail (Francis P. Ryan Section)

    6 Reviews

    Northampton, MA

    Norwottuck Rail Trail (Francis P. Ryan Section) is a hiking and biking trail in Northampton, Massachusetts. It is 2.6 miles long and begins at 146 feet altitude. Traveling the entire trail is ...
    •  2.6 miles

    Norwottuck Rail Trail (Francis P. Ryan Section) is a hiking and biking trail in Northampton, Massachusetts. It is 2.6 miles ...

  • #15 Southwest Corridor

    0 Reviews

    Boston, MA

    This urban rail-trail takes you from downtown Boston to Jamaica Plain. It is used by bicyclists commuting to and from downtown and by outdoor enthusiasts looking for some fun in the sun near ...
    •  5 miles
    •  Guide

    This urban rail-trail takes you from downtown Boston to Jamaica Plain. It is used by bicyclists commuting to and from downtown ...

  • #16 Great Barrington Cruise

    0 Reviews

    Great Barrington, MA

    The Great Barrington Cruise is adapted from the Great Josh Billings RunAground, a triathlon run every fall. This ride follows the triathlon's cycling course almost to Stockbridge. It then turns ...
    •  28.9 miles
    •  Guide

    The Great Barrington Cruise is adapted from the Great Josh Billings RunAground, a triathlon run every fall. This ride follows ...

  • #17 Bald Hill Road

    5 Reviews

    J. C. Phillips Sanctuary, MA

    Bald Hill Road is a hiking, biking, and horse trail in Boxford, Massachusetts. It is within J. C. Phillips Sanctuary (Lockwood) and J. C. Phillips Sanctuary. It is 1.3 miles long and begins at ...
    •  1.3 miles

    Bald Hill Road is a hiking, biking, and horse trail in Boxford, Massachusetts. It is within J. C. Phillips Sanctuary (Lockwood) ...

  • #18 Martha's Vineyard: Two Tours

    0 Reviews

    Vineyard Haven, MA

    Martha's Vineyard remains an island 'retreat' for beachgoers and cyclists alike. Its roads wind through woodland and farms, past miles of white sand beaches, around millponds, inlets, and creeks. ...
    •  24.7 miles
    •  Guide

    Martha's Vineyard remains an island 'retreat' for beachgoers and cyclists alike. Its roads wind through woodland and farms, ...

  • #19 Cohasset Coastal Ramble Ride

    2 Reviews

    Black Rock, MA

    The Cohasset Coastal Ramble explores the shoulder of land southeast of Boston where the coastline curves primarily from an east-west to a north-south direction. It is the first really nice stretch ...
    •  26.8 miles
    •  Guide

    The Cohasset Coastal Ramble explores the shoulder of land southeast of Boston where the coastline curves primarily from an ...

  • #20 Harold Parker Road

    4 Reviews

    Essex County, MA

    Harold Parker Road is a hiking, biking, and horse trail in Essex County, Massachusetts. It is 1.3 miles long and begins at 119 feet altitude. Traveling the entire trail is 2.6 miles with a total ...
    •  1.3 miles

    Harold Parker Road is a hiking, biking, and horse trail in Essex County, Massachusetts. It is 1.3 miles long and begins at ...