Looking for the best trails around Winchester?

Explore the best rated trails in Winchester, MA, whether you're looking for an easy walking trail or a bike trail like the Danvers Rail Trail and Swampscott Rail Trail . With more than 105 trails covering 620 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

East Bay Bike Path (RI)

East Bay Bike Path

November, 2023 by thejake91739

This bike path between Bristol and India Park in Providence was just what I had hoped for: picturesque views, charming towns and homes, beautiful foliage, and friendly people of all ages!

In addition, there were a few surprises. I discovered that this path is a definite paradise for bird lovers. It even passes right by an Audubon Nature Center accessible by the path! There were also many interesting historical aspects such as the Pomham Rocks Lighthouse, remnants of the old railroad, and the Squantum Association mansion. The best surprise and highlight for me was the Spooky Bottom Scenic Dock. Don't skip or miss this! I barely noticed the small sign for it. It's not spooky, and it's not a dock. It's a pier that will take you out into the bay for awesome views of the causeway, bay, and the Providence skyline including the state capital's green dome!

This path is obviously extremely popular with the community: walkers, joggers, bikers, dog walkers, and many parents pushing strollers. Also, I have never seen so many students on their way to school utilizing a path like this on their bikes. I must have seen at least thirty. That's a testament to the safety of the surrounding neighborhood and community!

I drove all the way from California to experience this trail, and I'm so glad I did. I've ridden my bike in forty-nine of our fifty states, and I definitely put this Hall of Fame trail in my top five favorites! A+, state of Rhode Island!

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!

Air Line State Park Trail

Hard packed surface

October, 2023 by sbridges7272

We love biking the Airline and have used non electric hybrid bikes as well as e-bikes. Both work well. On 10/28/2023 we biked the section from Willimantic parking at the Connecticut Eastern Railroad Museum area and pedaled to Rt. 207 Lebanon Rd, Amston, CT. FYI, we're in our 60s and encountered no difficulties with the terrain.

Accordion

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.

Washington Secondary Bike Path

The path is nice and cool in the summer due to lots of shade. Much of it has large sections of big tree roots, though.

October, 2023 by csebetes

The path is nice and cool in the summer due to lots of shade. Much of it has large sections of big tree roots, though.

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!

Rockingham Recreational Rail Trail (Portsmouth Branch)

Like so many, GREAT!!

September, 2023 by twelch11

This is a wonderful trail. But I must add that I am very fond of many of the rail trails in New Hampshire. My wife and I are old and use E bikes with fat tires for our rail trail trips. However, on this trip we passed several riders using road bikes with skinny tires, and they were doing just fine.

From the start of the trip at Lake Massabesic to the end at Ash Swamp Road, this trail proved to be a most enjoyable trail with very few spots that required a little caution. Leaving Massabesic the trail is wide, hard packed and easy going. Mostly wooded areas with many brooks, swamps and for the most part, great scenery.

There were very few muddy or wet areas but all of them were easily navigated. But keep in mind, this trail crosses a few very busy highways. Luckily the first three busy roads you will encounter have tunnels, so you don’t have to cross the roads. Out of caution we got off our bikes and walked them through the tunnels, but a good rider might not have to do that.

As you make your way east there are some very interesting sites like the Emerson Mill site and a couple others that might spark later trips. The trail goes past several lakes and large rivers with very interesting spots to stop for a break or a snack. As you move east you will approach the Star Speedway, (a small racetrack) but is not open during the morning or early afternoon time periods. Further on you will have to cross a very busy route 125. Buy don’t worry, there is a traffic light on either side of the road and all you must do is press the button and wait for the light to stop all the cars, very fast and simple.

There is a rail museum and ice cream spot if you need a break or sugar fix right on the trail, so it makes a stop easy and quick. Continuing east you finally make it to the eastern end at Ash Swamp Road. There is an old rail station that is under restoration there with plenty of parking and easy access. All in all, this is a great trip that shouldn’t be missed.

Northern Strand Community Trail

Talk about a fun (and visually stimulating) ride!

September, 2023 by tommikeleonard

This is a very fun and very well maintained trail. It crosses throught the heart of several cities/towns, so there is a lot to see. The trail is pretty flat for the whole duration, so it is an easy ride or walk.

Rockingham Recreational Rail Trail (Portsmouth Branch)

Beautiful woodsy trail with water features

September, 2023 by lvs_tl

I'd thought maybe this trail wouldn't be suitable for my road bike w/ slightly wider tires, but it worked out fine. Surface was mostly hard packed dirt/gravel, at least the 9 miles I rode starting at the southern end in Newfields. There were some muddy spots and a few rocks and roots to avoid, but never had to get off the bike and walk. Ponds, swamps, brooks and lots of woods. A few easy road crossings, no road noise on this part. Well worth a ride.

Monadnock Recreational Rail Trail

Pleasantly Surprised

September, 2023 by fyredown

Truly a nice ride this weekend. Packed surface, mixed terrain but nothing our Surly Ogre's couldn't handle. This was not a crowded trail but there were a spattering of walkers, bikers, dog walkers. Made you feel happy to be alive! Whoever is maintaining this trail - thank you!

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Accordion

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