Looking for the best trails around Gloucester?

Explore the best rated trails in Gloucester, MA, whether you're looking for an easy walking trail or a bike trail like the Swampscott Rail Trail and Spicket River Greenway . With more than 89 trails covering 453 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

Garrison Trail

DOGS NEED TO BE ON A LEASH

April, 2024 by inluvwsl

The trail itself is excellent. A great place for a leisurely walk, bike or skate between Newburyport and Amesbury with options to continue/connect to the rail trail for a longer trek. But while the trail is awesome, I don’t understand why people feel entitled to let their dogs roam off leash along the trail? This makes it not only uncomfortable for those walking, but dangerous for those biking or skating that don’t want to be chased by a dog, friendly or not, that can be the cause of an accident. It’s really not the dogs fault… it’s the owners ignorance and disrespect for anyone that shouldn’t have to alter what they are doing in order to be deal with your dog. If you want to walk your dog off leash, there are numerous other places nearby that can accommodate you.

Bruce Freeman Rail Trail

Great for training half and full marathon

April, 2024 by trishle9

There’s tons of long stretches of trail that doesn’t require you to wait for pedestrians signals. And not many major intersections stops. Trail is mostly flat with a few rolling inclines and declines.

Boxford Rail Trail

Nice extension to the Topsfield/ Danvers trail

April, 2024 by antiquecaddy

This is a nice trail. It can be a bit hard to ride with road tires, much easier with a hybrid. You often run in to walkers, the people who use this trail are always friendly. It is a Part of the East Coast Greenway and a nice extension to the Topsfield / Danvers trail. I have run into "through riders" doing some part of the East Coast Greenway.

Accordion

Garrison Trail

Nice Trail

April, 2024 by dvcummingsii

We did the first two miles from Park n Ride in Newburyport up until the intersection in Salisbury before returning back for the two mile trek back. Crossing over the Merrimack River 95 Bridge was beautiful. Recommend for all bikers but especially first time riders as it’s a smooth ride.

Reformatory Branch Trail

Too muddy

April, 2024 by res3737

The trail has some muddy patches. Most of them are manageable, except there is one spot immediately west of the Route 62 crossing where you will sink in up to your ankle and there's really no way to get around it.

Danvers Rail Trail

Easily traveled on foot or bike

February, 2024 by ckldy529

One of our favorite trails! Several locations to hop on or off the trail, whether you’re looking for a short walk or a more lengthy adventure. The swamp walk shouldn’t be missed. Enjoy ambling along the boardwalk through the swamp where you may see beavers, turtles, snakes or a great blue heron or two. I recommend parking at Choate Farm and following the well-marked wooded path through the woods to the rail trail. Kids love it!

South Manchester Rail Trail

Nice trail

December, 2023 by andtun1

I live in the area & have walked my dog using the section from S. Beech to Gold Street for years. A new section from Gold to Perimeter Road is finally completed as well. I can't wait to try the new section in the summer when I can ride my bike or rollerblade.

Nashua River Rail Trail

Nashua River Rail Trail

November, 2023 by thejake91739

I traveled all the way from California with high expectations for this trail and I wasn't let down (except for the repairs being made on the damaged portion of the trail). It's all good. I made it work.

What an awesome trail for a mid October bike ride!
- The colors of the trees reflected upon the numerous ponds and lakes.
- The pleasant chirping and squawking of active birds.
- Leaves fluttering gently to the ground.
- A wide, smooth path carpeted in golden brown leaves.
- Historic buildings.
- Industrious squirrels.
- Old, historic stone walls.
- Deep, dark woods.
- Rolling, grass covered hills.
- Harvested pumpkins on a farm being sorted into bins.
- Goats, horses, and the friendliest trail users you could ever hope to cross paths with!

I took a leisurely four hours out and back and over 200 photos and video to capture my wonderful memories of this trail. Thank you Massachusetts and New Hampshire!

Watertown-Cambridge Greenway

No Parking

October, 2023 by mpmcdonald_tl

Contrary to the symbol on the map, parking is NOT available at the Fresh Pond end, even on Sundays, unless you live in Cambridge, and even then, "Permit Required". I drove almost two hours to get there and back, and never got to walk it.

Rockingham Recreational Rail Trail (Portsmouth Branch)

Smoother ride from Newfields end

October, 2023 by rf0595

My brother and I had no problem riding this beautiful trail on e-bikes with 1 5/8 inch tires on a weekday in Sept. 2021 and again in August 2023. Both times we rode west from Newfield and noted that the trail has noticeably more rocks as we headed west of Raymond. We were glad we had front suspension forks. Dearborn Forest just past Onway Lake was our turnaround point at about 17 miles. At Route 125 (Main St.) in Epping, be sure to take the right trail at the fork to continue on the Portsmouth branch. The left trail is the Fremont Branch where you may find yourself riding with ATV's.
At Freetown Road (Route 102) in Raymond, McDonalds is just south of the trail. If you are looking for a tastier burger and have more time, go north one block on Route 102 to Route 27 (Hannaford on your right), then go left one block to Tuckaway Tavern & Butchery (featured on Guy Fieri's "Diners, Drive-Ins and Dives" television series).

Bruce Freeman Rail Trail

Fantastic Trail, can be a little congested in areas

October, 2023 by dianei

I have ridden this trail many times, and always enjoy it. It is well maintained, well marked, plenty of great places to park for a variety of stop/starting points. Several lovely bridges over roads that would be difficult or impossible to cross. A bike shop along the route, even EV charging stations at the lot by the West Concord train station, where you can also visit the lovely shops and cafes nearby!

Be aware that the section from West Concord towards the Sudbury expansion is well used by the nearby Middle school for after school activities and can be heavily congested during that time. Road cycling can be a challenge weekday afternoons when school is in session.

Nashua River Rail Trail

Great Trail w/recent storm damage

September, 2023 by dianei

First: be aware that a recent storm has washed out a section of the trail about 2 miles from the Ayer parking lot in Sept 2023. People are portaging past it, but some set-ups might not work in this situation. That said, this is a great trail. Plenty of parking at many points along the way, some even have EV chargers!

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Accordion

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