Looking for the best trails around Brewster?

Explore the best rated trails in Brewster, MA. Whether you're looking for an easy walking trail or a bike trail like the Old Colony Nature Pathway and Bridle Trail . With more than 16 trails covering 88 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

Shining Sea Bikeway

A visual gift to the mind !

August, 2022 by carlynefournier

The shining seas bake trail (from N Falmouth to Woods Hole ) is absolutely stunning ! Gorgeous! It is such a treat for the visual and a gift to your mind! It so peaceful and the best 25 miles ride i have done in a long time. You will bike through several different landscape types/ views, including woods, cranberry field, salt marsh and the ocean. Bring a sandwhich to picnic by the ocean, or stop at the rail way cafe ( along the path) or my fav the Pie in the Sky Bakery & Cafe in Woods hole for an amazing chicken or tuna salad! Enjoy!

Cape Cod Rail Trail

The Best…..

August, 2022 by gulfstreambents

…..Rail Trail on the NorthEast Coast in our opinion. We visited for the fourth time and stayed several days in Orleans, MA for the sole purpose of riding this Trail and did so several times. Easy access to the Trail from our hotel (The Cove Motel, highly recommend). Perfect pavement. Riding South and West the first day through varied scenery including Cranberry bogs and even a beautiful beach. From the roundabout you can access the Old Colony Trail. Don’t miss stopping for Ice Cream at Ferretti’s Market (I think). Home made ice cream for $5 a serving, not a scoop!!!! Best I’ve ever had. The extreme west end becomes a bit desolate as you pass the Blue Rock golf course. The following day we cycled North from our base in Orleans to the new end point 1 mile north of the original. Easy access from several places to the beaches and worthwhile for the view even if you don’t swim. SHARK WARNINGS POSTED.

Cape Cod Rail Trail

Brewster to Orleans

July, 2022 by tsyrell

First time on this trail, I did about 11 miles centered from Nickerson Park. I enjoyed the ride, but did notice it was bumpy. Overall, it was a good trail, but could use some updates to minimize the bumps in the pavement.

Accordion

Norwell Pathway

Best of the South Shore

July, 2022 by rhylandkeller98

I fell in love with running on this trail. Paved with a few wooden bridges. Rarely too crowded, and nice shade underneath the trees. Some elevation change toward the end, but nothing extreme. The pathway itself isn’t super long, but there are lots of roads nearby that it branches off into. Highly recommend going for a run/walk here in autumn!

Mattapoisett Rail Trail

Straight ride through some beautiful scenery. Really short but a great ride none the less.

June, 2022 by boredness113

Straight ride through some beautiful scenery. Really short but a great ride none the less.

Old Colony Rail Trail

Excellent trail w/ a bonus

June, 2022 by andrix

We entered this trail off the Cape Cod Rail Trail on our E-Bikes. Trail was in fine condition with interesting views along the way. The bonus was the Chatham road loop which takes you along the ocean and by the Chatham lighthouse. There's a map at the end of the Old Colony trail for this loop but we needed our trusty GPS to keep us on track.

Province Lands Bike Trail

Beautiful fun ride

June, 2022 by andrix

There's definitely hills on this trail. We rode our E-Bikes and had a great time. All the spurs led to interesting spots. The trail looked and felt like it had just been recently paved. Recommend parking at the National Park Visitors Center lot trailhead. BTW - The Visitors Center has an elevated platform that gives an excellent viewpoint to the area.

Cape Cod Rail Trail

great ride!

June, 2022 by 2lovinthejourney

We rode from Sweetwater Campground down to the roundabout. From there we took the Old Colony Rail Trail to Hangar B Eatery at the Chatham Airport. Great food! Great ride! Downside is the business and road crossings. But…it is a vacation spot. Spots along the way with walking paths and picnic tables.

Old Colony Rail Trail

nice…but busy.

June, 2022 by 2lovinthejourney

Great trail. Level path for most part. Does get very busy with walkers and kids. Lots of stopping to cross road. Lots of paths to hop off bike and do some walking. A few picnic areas along the way also. At the trailhead there is an awesome place to grab breakfast or lunch: Hanger B Eatery. It is located at the Chatham Airport.

Phoenix Bike Trail

Short & Sweet

May, 2022 by oxlilemmiexo

Short ride but the path is well maintained and good scenery along the way. Some of the trail is closed right now and a downside is there weren't any place to stop along the way for coffee or lunch or good view at the end points.

Shining Sea Bikeway

From one end to the other the trail is filled with amazing views from the ocean to the to ponds nature bogs marshes shops just off the trail. Walking trails bird watching a great bike shop at the end of the north end of the trail.

April, 2022 by almakino

From one end to the other the trail is filled with amazing views from the ocean to the to ponds nature bogs marshes shops just off the trail. Walking trails bird watching a great bike shop at the end of the north end of the trail.

Cape Cod Rail Trail

Start to Finish

October, 2021 by smithdj

My wife and I rode the full 27.5 miles on 10/15/21. We started at the western most trailhead (near Homer Park) and rode to Wellfleet and made a delightful stop at PB Boloulangerie Bistro for a treat before heading back to the Home Park trailhead. 55+ miles and the only criticism would be that the asphalt may not have been put in think enough to withstand the tree roots that are undermining the trail. The jarring from the roots becomes somewhat annoying after a while. We would ride it again though!

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Accordion

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