Looking for the best trails around Osterville?

Explore the best rated trails in Osterville, MA, whether you're looking for an easy walking trail or a bike trail like the East Bay Bike Path (RI) and World War II Veterans Memorial Trail/Norton Rail-Trail . With more than 23 trails covering 183 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Nantucket Multi-Use Paths

Fragmented Trail

October, 2025 by jeff.steele

If you notice the RTT Map you will notice the island bike path is badly fragmented. A Bike Path ends & no signage to show where it picks up again. It will spit you out on a busy highway making it a nerve racking ride not knowing how long you will be in the middle of the busy highway. Be safe!

Province Lands Bike Trail

perfect!

September, 2025 by chleary11

Did this in August. The trails are well kept, a bit challenging but the views are incredible! You can ride right into ptown and avoid parking hassles and expense.

World War II Veterans Memorial Trail/Norton Rail-Trail

Trail is well maintained, very few bumps, and flat. It's listed as 6.6 miles long but I clocked it at closer to 7.5 miles. I gave it 4 stars because it's not really a very scenic trail.

August, 2025 by gconner02019

Trail is well maintained, very few bumps, and flat. It's listed as 6.6 miles long but I clocked it at closer to 7.5 miles. I gave it 4 stars because it's not really a very scenic trail.

Accordion

Shining Sea Bikeway

summer crowds plentiful

August, 2025 by hz45mrq5bv

Went on a ride just after 1pm. There were a lot of people. Some are so clueless that there are others that might want to use the trails. On a 90 degree day there were kids path side selling cold drinks and ice cream. At least they are out of the house. Path condition was nice. The path is maintained nicely and it’s clean. Wish there was a trash a can of two or few along the path as I saw many doggie poop gabs just left on the side of the path. Over all it was a good ride. Next time I would go in the morning or late evening to see how the crows is. Enjoy!

East Bay Bike Path (RI)

a great goes through beautiful surroundings

August, 2025 by jhoff1

It is such a lovely trail. The view is gorgeous, either from the ocean or from the land. It goes through a few towns, all lovely and friendly. There are shops along the trail for you to stop by for ice cream, coffee or lemonade. There are a few road crossing, but the cars are very friendly and stop to let cyclists cross. The destination Bristol is just beautiful! Some areas are in the open, so the wind can be your friend or not …..

East Bay Bike Path (RI)

nice paved path

August, 2025 by rdpd2025

It’s a nice paved path, shaded half way through. Good for families with kids. Parking is free but though to find, suggests keep following the path till you find parking. There are several options along the way from the eastern end of the trail. Few food and restroom options, within coffee or mall shops. Public restrooms are very limited at least when starting from east end. We went only half way and back, with kids. Looking forward to finish the second half soon.

East Bay Bike Path (RI)

Very good for in line skating

July, 2025 by andrew.magruder

I’ve skated every inch of this path dozens of times over many years. There’s a badly done asphalt patch at mile nine plus 100 yards (from the south end) that has a sharp lip that can face plant you. There are a fair number of root heaves that need your attention but can be skated or stepped over. There’s a public bathroom in the lobby of the Warren police station 150 feet from the trail (around mile 4 from the south end). Walk up the stone stairs from Joyce St.

East Bay Bike Path (RI)

variety

July, 2025 by maxpanter

Thoroughly enjoyable, three hour ride, passing chest at the beach, through neighborhoods, wildlife conservation areas, and over bridges. The Bristol parking lot is being redone and cannot be used, but we found parking on the streets. There were at least two detours in Barrington, but that made it only more exciting. only nice people on the trail and drivers stopped very politely at every of the many intersections. Overall, this ride was a pleasure and worth the 1 Hour drive to get there.

East Bay Bike Path (RI)

Bristol and Beyond

July, 2025 by mt8vrd945v

What a perfect ride on a Monday afternoon. Delighted to stop at Plant City for refreshments before we turned around and headed back to Bristol.

Hanover Branch Rail Trail

Nicer Trail

July, 2025 by jafischer23

Better for walking or running than biking. The parking at Ellis Field works OK but isn't the best location for that end of the trail, you have to ride down Circuit Street to get to the trail at 139. Better to park in the small lot off of 139 at Circuit Street if you can.

Phoenix Bike Trail

My Favorite Trail

June, 2025 by james.w.carney.civ

I grew up in Fairhaven and moved away, but return every summer; the highlight of my trip being time spent on this bike trail and the Mattapoisett leg of it. Lots of “branches” if you want rack up some serious miles; Weeden Road, Gillette Rd, Mattapoisett Neck Road and continuing down Front (?) Street in Mattapoisett to Ned’s Point Lighthouse. Couple detours on the Fairhaven part and a stretch about a 10th mile that’s dirt and not conducive to a road bike. a 10th of a mile

Phoenix Bike Trail

connects to Mattapoisett

June, 2025 by teamfiona

The Mattapoisett portion is open. It is a seamless continuation of the phoenix path and is very pretty, well maintained, and has a beautiful boardwalk near the end. It goes to a beach and you can then ride on a quiet road to Ned points lighthouse. Definitely worth the trip.

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Accordion

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