Looking for the best trails around Southwick?

Explore the best rated trails in Southwick, MA, whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Mattabassett Trolley Trail . With more than 51 trails covering 434 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

Ashuwillticook Rail Trail

Great fall ride.

November, 2023 by cantabty

Excellent experience on this fresh paved trail. The scenery of the ponds and mountains in the distance was worth the trip.

Bloomfield Greenway Multi-Use Trail

Extension to Tariffville is complete

November, 2023 by bcgp

A sidepath has been constructed adjacent to Route 189 to Main St in Tariffville. Trail is now about 3 miles long. It will be designated as part of the East Coast Greenway and is visible on Google Street View.

Farmington River Trail

Farmington River Trail

November, 2023 by thejake91739

After reading many of the mixed reviews for this trail on TrailLink, I decided to keep my ride short but sweet by restricting it to what seemed to be the most picturesque - the portion between the historic Unionville train depot and the Riverside Nursery and Garden Center in Collinsville.

This part of the trail contains breathtaking views of the officially deemed wild and scenic Farmington River. In addition, since I did this in mid October, the river was a perfect reflecting glass for the amazing fall colors.

My ride was only a total of twelve miles out and back, but I now have the most perfect photos, videos, and memories of this Connecticut treasure!

The bike ride is easy and mostly flat with lots of locals getting their steps in and exercising their dogs. Surprisingly, I only encountered two other bicyclists on my early weekday morning ride.



Accordion

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.

Harlem Valley Rail Trail

flat . smooth. gorgeous

October, 2023 by lindarkv

I rode the southern half of this trail from Millerton to Wasaic the first week in October on a 75° afternoon. Beautiful ride on a beautiful day.

CTfastrak Multi-Use Trail

very quiet road

October, 2023 by cvt5szrnsg

Nice quiet ride to take time to enjoy these beautiful days.

Harlem Valley Rail Trail

Serene and lovely

September, 2023 by raresparky

Rode the 13 miles from Orphan Farm Rd to Millerton and back. At the northern end, at Orphan Farm Rd is a large parking area adjacent to a small farm, a solar panel field and a glamping site. No one there at 8am that Saturday but half a dozen cars upon my return at 11. Likewise, I had the trail practically to myself until I neared Millerton and found it moderately traveled by later that morning. The asphalt trail was in very good condition and there are a few boardwalk sections as well, also in very good condition. The environs are beautiful with forested sections, farm fields, wetlands and vistas of the nearby hills. Not more than two miles from the north end is the Depot Deli, near the entrance to Taconic State Park, where all manner of beverages, ice cream and snacks can be found. Breakfast at Oakhurst Diner in Millerton is highly recommended. Clean public bathrooms can be found just behind the schoolhouse museum beside the trail after crossing the main street.

Ashuwillticook Rail Trail

Good scenic ride

September, 2023 by richmedcraft

I rode the trail from Pittsfield to the end in North Adams and back on 8/5/23. The trail is paved and in good condition and restrooms at the Pittsfield trail head were clean and working fine. Nice scenery including lakes and the Berkshires- I was able to finally identify Mt Greylock after the morning clouds had dissipated. The grade is gentle and I was able to keep up a consistent pace for the ride.

Southern New England Trunkline Trail

Beautiful Trail

September, 2023 by robynkeys

We biked the trail today from Franklin and although it was a beautiful ride through the forest, our trip ended at the 4 mile mark because the path turned into a single lane rocky/sandy pathway. We traveled it briefly but it was not doable. It’s frustrating after reading from several apps and websites that it did not mention this. They all state it’s a 22 mile ride. Still had fun. Love getting out on our bikes!

Ashuwillticook Rail Trail

great trail

September, 2023 by dpwrztjhrw

Asphalt smooth and trail is terrific. Easy, flat trail with some water views passing Silver Lake/Pittsfield.

CTfastrak Multi-Use Trail

Good for transportation and exercise, not all that scenic

August, 2023 by sjwang40

I think folks have to temper their expectations. This isn't the Farmington Canal Trail and isn't trying to be. This is a nice, well paved track for exercise and actual transportation. It provides a bike link from Newington and the southern end of West Hartford to downtown New Britain that previously didn't exist. For that I'm super happy. West Hartford has a decent bike network that connects into Hartford, so now there is a semi-cohesive bike network that spans from downtown Hartford all the way to New Britain with stops in between. New Britain is booming (by New Britain standards) so there's actually a lot to visit at the end of the trail, like the art museum, breweries, restaurants, etc. I wish the Multi-Use Trail extended all the way to the Elmwood or even Hartford stops, but it's useful the way it is now. It's not all that scenic but there's still a decent amount of greenery and it's pleasant to ride. It's next to the busway and train tracks, but the train is relatively far away, and the buses are not noisy or especially polluting (they are hybrids).

Columbia Greenway Rail Trail

awesomeness!!!

August, 2023 by lexibug73

So amazing to be back on our bikes again. The hubby and I tried this trail for our first with our new bikes. Smooth ride… great views over the Westfield River. Definitely one to try when going out for your first ride!

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Accordion

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