South Shore

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Miles and miles of quiet backcountry roads with short hill climbs, ocean views, and historical Pilgram-era attractions.

Written by

Eric Gilbertson


20.0 miles

The mileage depends on the route taken, but would generally be between 10-100 miles. A reasonable average could be 20 miles.

Destination Distance From Downtown

34.3 miles


3 of 5 diamonds

Cycling trips can be made longer to be more difficult or shorter to be easier.

Time To Complete

1 days

Day trips are the most popular outings on the South Shore, though 2-day overnight trips are also fun.


Spring, Summer, and Fall

Summer is the best time for the warmest weather and longest days, but Spring and Fall are fun as well. Winter may be too cold and snowy for most cyclists.

Dog Friendly


Fees Permits


Land Website

Map My Ride Routes



The south shore region extends roughly from Boston to Plymouth along the coast of the Atlantic Ocean, and is a popular day-trip and weekend cycling location. Hop on your bike anywhere in Boston, head for the coast, and follow quiet backcountry roads as far south as you please. There are many distractions along the way, of course, from short hikes at World’s End and Wompatuck State Park, to quick dips in the ocean at Nantasket Beach, a historic lighthouse at Scituate, and the famous Plymouth Rock of the Pilgrims’ days in Plymouth.

If you prefer to put on a lot of miles you’ll have no problem getting a good workout with the continuous rolling hills along the coast boosting your heart rate.

What Makes It Great

The scenery, quiet back roads, and history are what make the South Shore popular with cyclists. Many different route options keep people coming back. If you bike out to the tip of Hull Point you get a panoramic view of the ocean, the harbor islands, and the Boston skyline, plus excellent swimming opportunities at the nearby Nantasket Beach. South to Plymouth on 3A you pass through wooded hills and can see the famous “1620” carved in Plymouth Rock on the beach. Hug the coast on more rural roads and you get views of the ocean, even seeing the shores of Cape Cod across the bay if the skies are clear.

One-way trips are no problem with the bike-friendly MBTA commuter rail making numerous stops between Boston and Plymouth. Just bike down as far as you want and take the train back to Boston afterwards.

Overnight trips are also an excellent idea. Throw your tent and sleeping bag in some panniers and head down to Wompatuck State Park or Myles Standish State Forest to spend the night. Then cycle or take the train back to town. Or, if you're more adventurous, continue biking past Plymouth to the end of Cape Cod on the popular Boston-Provincetown route. Then catch a ferry from Provincetown back to Plymouth or directly to Boston for a big loop. Ferries generally run only in the summer, but check schedules at

Who is Going to Love It

Any cyclist interested in great ocean scenery just outside of Boston, or in a pedal-powered tour of historic Massachusetts will enjoy the South Shore. Those interested in a good workout will find ample miles of hills and bike-friendly roads to choose from. Cyclists training for longer distance or cross-country tours will enjoy the camping opportunities not far from town.

Directions, Parking, & Regulations

The main cycling road on the South Shore is 3A, running from Quincy to Plymouth, with smaller side roads more closely hugging the coast and heading to destinations like Hull Point. Parking is available at most public beaches, town centers, and Commuter Rail train stops. If planning to take you bike on the Commuter Rail on a weekday, ensure that you avoid peak hours when bikes are prohibited. (Generally 5-9am inbound, 4-7pm outbound, but check for more details).

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South Shore

70 Water Street
Plymouth, MA, 02360
41.957988, -70.662157

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