Road Bike

The Best Road Bike Trails in Massachusetts (United States)

996 trails

Photo of Phoenix Bike Trail (Fairhaven) Photo of Mass Central Rail Trail, MA Photo of Wellsfleet Pier to Great Island Trailhead ( and Uncle Tims Bridge)
  • Mass Central Rail Trail, MA

    Road Bike
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    near Oakdale, Massachusetts (United States)
    Distance
    8.57mi
    Elevation +
    262f
    TrailRank
    23
    Photo ofMass Central Rail Trail, MA

    We biked the Mass Central Rail Trail near Holden in eastern Massachusetts in August 2021. Click "View more" below for bike info.

  • Oak Hill - Yellow Trail

    Road Bike
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    near Shaker Village, Massachusetts (United States)
    Distance
    3.36mi
    Elevation +
    266f
    TrailRank
    22

    Good loop that'll take you less than an hour on a bike. There are a few more technical parts that keep it fun, and some exposure at the chasm - but overall it's fairly straightforward. If you're not comfortable riding th...

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  • Canaan

    Road Bike
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    near Canaan, Connecticut (United States)
    Distance
    41.67mi
    Elevation +
    1463f
    TrailRank
    19

    This is a lovely ride through pastoral country in the Southern Berkshires. There is little traffic (like one car every few minutes during the week) except on the short section of US Route 7. This is a popular weekend des...

  • North Central Pathway, MA

    Road Bike
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    near Winchendon, Massachusetts (United States)
    Distance
    18.98mi
    Elevation +
    302f
    TrailRank
    19
    Photo ofNorth Central Pathway, MA

    We biked the North Central Pathway, near Winchendon in northern Massachusetts, in October 2021. Click "View more" below for hike info.

  • Callahan Green Loop

    Road Bike
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    near Nobscot, Massachusetts (United States)
    Distance
    7.18mi
    Elevation +
    453f
    TrailRank
    19
    Photo ofCallahan Green Loop

    Easy loop around Callahan, with a challenging climb to finish it off. Don't cross the road if you don't want to do the climb.

  • Cape Cod Canal Bikeway, MA

    Road Bike
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    near Buzzards Bay, Massachusetts (United States)
    Distance
    15.13mi
    Elevation +
    3f
    TrailRank
    19
    Photo ofCape Cod Canal Bikeway, MA

    We biked the Cape Cod Canal Bikeway in eastern Massachusetts in October 2021. Click "View more" below for hike info.

  • Clipper City Trail, MA

    Road Bike
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    near Newburyport, Massachusetts (United States)
    Distance
    16.07mi
    Elevation +
    118f
    TrailRank
    19
    Photo ofClipper City Trail, MA

    We biked the Clipper City, Marsh and Ghost trails near Newburyport in northeast Massachusetts in June 2021. Click "View more" below for hike info.

  • S. Mass N Ct 65 loop

    Road Bike
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    near Ware, Massachusetts (United States)
    Distance
    68.30mi
    Elevation +
    4721f
    TrailRank
    16

    I did this ride 6-4-11 immediately after the devastating tornado of June 1st. I was awestruck at the damage in Monson and Brimfield

  • Natick tour

    Road Bike
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    near South Sherborn, Massachusetts (United States)
    Distance
    41.82mi
    Elevation +
    5499f
    TrailRank
    16

    Trip around Natick till Reservoir hill and Rodhe Island. Thanks Bob for the bike and experience. Total time of 3h considers some pause we made to wait for some colleagues. Cycling time was around 2h30min. Elevation see...

  • Oak Hill - Blue Loop

    Road Bike
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    near Littleton, Massachusetts (United States)
    Distance
    1.21mi
    Elevation +
    190f
    TrailRank
    9

    Very quick 1 mile loop (I also add the lookout rock at the top). Counter-clockwise seems the best to get some flow on the way down.

  • Côte du New Hampshire

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    near Plum Island, Massachusetts (United States)
    Distance
    44.32mi
    Elevation +
    213f
    TrailRank
    33
    Photo ofCôte du New Hampshire Photo ofCôte du New Hampshire Photo ofCôte du New Hampshire

    Départ du Camping Salisbury MA, remonté la côte du New Hampsire en passant par Hampton Beach juaqu'à Portsmouth

  • charles river

    Road Bike
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    near Back Bay, Massachusetts (United States)
    Distance
    13.48mi
    Elevation +
    112f
    TrailRank
    32
    Photo ofcharles river Photo ofcharles river Photo ofcharles river

    Boston MA USA

  • Plum Island Pointe

    Road Bike
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    near Salisbury, Massachusetts (United States)
    Distance
    21.36mi
    Elevation +
    157f
    TrailRank
    32
    Photo ofPlum Island Pointe Photo ofPlum Island Pointe Photo ofPlum Island Pointe

    Peu sefaire à partir du camping deSalisbury Parc, tour de la baie de la rivière Mérimack. Le tour de la presqi'île Plum Island se fait dans un pars (payant), c'est un allé/retour sur un chemin de gravier plus approprié p...

  • Glouchester MA

    Road Bike
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    near Gloucester, Massachusetts (United States)
    Distance
    20.36mi
    Elevation +
    577f
    TrailRank
    31
    Photo ofGlouchester MA Photo ofGlouchester MA Photo ofGlouchester MA

    Tour de la péninsule à partir du centre ville de Glouchester en passant par Rockport, Belle randonnée sur le bord de l'eau.

  • Boston-Watertown a/r

    Road Bike
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    near East Cambridge, Massachusetts (United States)
    Distance
    19.02mi
    Elevation +
    46f
    TrailRank
    26
    Photo ofBoston-Watertown a/r

    Piacevolissima passeggiata sulla ciclabile lungo il fiume Charles, da Cambridge, passando davanti all' università di Harvard, fino alla graziosa città di Watwrtown dove si pedala in tranquillità tra stradine secondarie e...

  • Harwich Port

    Road Bike
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    near Harwich Port, Massachusetts (United States)
    Distance
    12.02mi
    Elevation +
    217f
    TrailRank
    22
    Photo ofHarwich Port Photo ofHarwich Port Photo ofHarwich Port

    Harwich Port bike path past some ponds. Rather crowded on the path on this hot sunny day.

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