Keystone Arch Bridge on Keystone Arch Bridges trail

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The Keystone Arch Bridges hiking trail is the perfect destination for a spectacular outdoor adventure in the Berkshires of Western Massachusetts. Walk through the remote woods and discover a series of stone arch bridges beside the trail. These bridges offer an architectural history to go along with the scenic views along the trail. This hike is a splendid addition to any Berkshires’ outdoor itinerary.

What is the Keystone Arch Bridges Trail?

river on  Keystone Arch Bridges trail
Westfield River from the train tracks

The Keystone Arch Bridges trail is next to the path of the Western Railroad built in the 1840s to move people and resources between Boston and Albany. The project required many bridges across the winding Westfield River. Therefore, the railroad builders constructed a series of practically indestructible stone arch bridges. As a result, the railway was the longest and highest one in the world in 1840.

Interestingly, the 70-foot high arch bridges are built without mortar or steel. They are a true engineering marvel with stones fitted carefully to hold up the entire structure. A keystone at the apex of the arch holds the whole thing together. This photo shows the keystone rocks up close.

Keystone on  Keystone Arch Bridges trail
A Keystone Arch Bridge–note the keystones at the peak of the tunnel

Of the original 10 arch bridges spanning the Westfield River, 5 remain. The rest were swept away in a flood or were dismantled when the railroad track path was changed.

The trail spans the town of Middlefield in Hampshire County, with portions in Chester in Hampden County and Becket in Berkshire County. The trailhead is located 2.5 miles north of the town of Chester on Middlefield Road. An interpretive sign telling the history of the bridges is at the trailhead parking lot.

Hiking the Keystone Arch Bridges Trail

The hike on the KAB trail is 2.5 each way. Numerous side trails leading down to the stone arches can extend the distance. Therefore, plan to spend a complete half-day or more exploring the trail and photographing the arches.

The beginning part of the trail features a waterfall beside the trail where a side stream enters the Westfield River. A clear side trail takes you down to the Double Arch, an imposing architectural beginning to your adventure.

Double Arch bridge on  Keystone Arch Bridges trail
Double Arch

The trail continues through beech-maple forest past the old house stone foundations so reminiscent of the Berkshires. I almost expected to turn the corner and see a maple sugaring shack.

trail in woods - Keystone Arch Bridges trail
Keystone Arch Bridges trail past old stone foundations

Gator Tooth Arch comes into view next. This concrete arch bridge was built to bypass the original stone bridge to the east. Active train tracks can be seen on the bridge.

railroad tracks on  Keystone Arch Bridges trail

The KAB trail then widens to follow the Old Pontoosic Turnpike, an ancient stagecoach route to Albany, NY. The 65-foot arch is next, followed by the 70- foot arch at the end of the trail. Information kiosks spread along the way interpret the natural area and the bridges.

The trail is rocky but is family-friendly. Leashed pooches will enjoy the stroll too. Organized hikes, lead by locals, to highlight the area are periodically available. Check the website for details.

Arch bridge with trees on the  Keystone Arch Bridges trail
Gator Tooth Arch bridge

Other Outdoor Adventures near the Keystone Arch Bridges Trail

Mountain biking

The KAB trail is a moderate ride for mountain bikers. A combination of single and double track alternates. It’s not a lot of miles but it’s still a fun way to see the bridges. The trail can be wet in spring and early summer. Therefore, please avoid it then to prevent erosion.

Winter adventures

Seeing the keystone arch bridges coated in white is a real treat. Similarly, the frozen ice cascading from the waterfalls and bridge abutments is spectacular. With the proper equipment, the Keystone Arch Bridges Trail is a fine winter hiking destination. I recommend microspikes as the trail can be icy. For more tips on winter hiking visit my post here.

Whitewater paddling

The Westfield River is the only federally designated Wild and Scenic river in Massachusetts. For good reason, it’s a whitewater jewel flowing through some of the most remote parts of the Berkshires.

whitewater river
Westfield River rapids

The West Branch of the Westfield runs through the arch bridges. In the spring, this section is a challenging roller coaster ride for experienced paddlers. The section is rated Class 3-4 whitewater. The paddling trip starts the town of Bancroft with the take-out at Chester.

If you are not yet a skilled paddler but still have a hankering for whitewater, visit the paddling mecca of the Deerfield River north of here. Several outfitters offer whitewater rafting and kayak instruction on the Deerfield River in the Berkshires.

Caboose camping

inside of a caboose
Caboose glamping

Yes, that’s right! You can sleep overnight in a train caboose to fulfill your childhood dreams. The Chester Railway Station & Museum rents an authentic 1921 wooden caboose located next to an active railroad for a totally unique glamping experience. Even if you don’t favor a berth in a train, a visit to the station museum with so many interesting railroad artifacts is in order. The museum is open on Saturday and Sunday from July to September.

old railroad trail
Chester Railway Station and Museum

Places to Eat Nearby the Keystone Arch Bridges Trail

Carms restaurant and coffee shop

white restaurant building

Carms is a former gas station on historic Route 20. Homemade is the keyword to use when describing this breakfast and lunch coffee shop in Chester. Homemade bread and pastries add to their generous farm breakfasts. Try their healthy and delicious homemade veggie burger. Add sinfulness by opting for the tater tots.

Chester Common Table restaurant

The same couple who own Carms runs this community-focused dinner restaurant. They feature locally sourced products at the restaurant. It’s a great place for a pint of craft brew or cocktail and your favorite comfort food. Check their calendar for entertainment by talented musicians from the area.

Accomodations near the Keystone Arch Bridges Trail

If you’re not onboard with caboose camping, try a Chester Airbnb.

Riverfront Getaway is a sweet 2 bedroom Airbnb located a few minutes away from the trail. It has a deck right on the river and has a hot tub. Is there anything better than a soak in a hot tub after an exhilarating day on the trail?

deck near river
Riverfront Getaway Airbnb-Airbnb photo

Check out the historic Haley House, if you need more space for family and friends. Step back in time in this 1910 period colonial home. Walk to all the restaurants and sites in the picturesque town of Chester.

sign on house
Haley House Airbnb-Airbnb photo

Wrap Up of the Keystone Arch Bridges Trail

The Keystone Arch Bridges trail is a splendid day hike for everyone. However, if you want more Berkshire charm and fresh air, make a weekend out of your time in the hilltowns of Western Massachusetts. There are many more hikes in Chester Blandford State Forest. The Appalachian Trail running through the spine of the Berkshires is a bit to the west. This area is the most wilderness part of Massachusetts so enjoy the many outdoor adventures you will find.

Certainly, other outdoor adventures in Western Massachusetts abound. However, a Keystone Arch Bridges trail hike will be a highlight of your time in the Berkshires.

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53 Comments

Sue Tippett · November 13, 2020 at 7:06 am

Loved this blog. Made me want to go and see these spectacular arches. Of course the idea of a night with a hot tub after a day of hiking is also really appealing. Wish I had known about the caboose glamping when I worked at the middle school as my train obsessed students would have loved learning about that. Thanks for all this great info.

    Karen · November 20, 2020 at 9:45 pm

    Thanks, Sue, Why did I know you’d like the one with the hot tub. You’d love this trail.

Pete Notclark · November 13, 2020 at 7:24 am

When they first proposed building this railway, potential investors scoffed at the absurdity of this engineering feet. One compared this stretch of railway to building a railroad to the moon.

    Karen · December 12, 2020 at 2:36 pm

    I guess that made it to the moon then. Thanks for the photos, Pete. They are so awesome.

Yeti · November 13, 2020 at 7:52 pm

Yayyy love the keystone Arches! Such a cool way to tie in history. I also like the KAB Trail because it’s my moms, your, nickname which was KBA. The caboose cabin also looks really cool there’s no time like now then to find isolated notes to Tuckaway. Please reach out to find out about the latest Burlington North Cove mini cabin project we’re putting together

    Karen · December 12, 2020 at 2:37 pm

    We need a family trip to this trail. No Noonmark potential, just easy hiking.

Shannon · November 13, 2020 at 9:03 pm

This looks like a great place to explore, and I’d love to stay in the caboose!

Sharyn · November 13, 2020 at 9:41 pm

Great post. This looks like such an interesting and enjoyable thing to do!

    Karen · December 12, 2020 at 2:45 pm

    Thanks, glad you liked it.

Kelly · November 13, 2020 at 9:45 pm

omg what a beautiful trail and I really want to go caboose camping and white water paddling. Both sound insanely fun! Thanks for sharing!

    Karen · December 12, 2020 at 2:46 pm

    The white water on the Westfield is awesome and the scenery even better.

Albi · November 14, 2020 at 4:24 am

Awesome post, really like this old infrastructure, bridges like this are really magical. Hope to see it soon

    Karen · December 12, 2020 at 2:47 pm

    Thanks. hope you get there.

Megan · November 14, 2020 at 11:14 am

What a cool place to hike! I especially love the idea of sleeping/glamping in an old caboose! What a cool experience that would be!

    Karen · December 12, 2020 at 2:48 pm

    Everyone loves the caboose idea. For good reason, I think.

Cindy · November 14, 2020 at 12:04 pm

Great post! I would love to hike along this trail and see all these amazing arches along the way. I also love the idea of caboose camping! That sounds like so much fun!

    Karen · December 12, 2020 at 2:49 pm

    Hiking on an awesome trail and then camping in a caboose. What’s not to love?

Margie · November 14, 2020 at 1:13 pm

Just saved the Keystone Arch Bridges Trail! I live in Connecticut, so hopefully, I can make it there soon.

    Karen · December 12, 2020 at 2:38 pm

    It’s definitely worth doing and not far from CT.

Cosette · November 14, 2020 at 3:13 pm

Great to read about the trail and history of the arches.

    Karen · December 12, 2020 at 2:40 pm

    I did find the history as fascinating as the hike.

Elena Pappalardo · November 14, 2020 at 3:45 pm

This hike looks so beautiful! Will definitely need to check it out next time in The Berkshires!

    Karen · December 12, 2020 at 2:40 pm

    Definitely. You would get some great photos.

Krista · November 14, 2020 at 6:04 pm

This looks like the perfect area to spend a day hiking in the fall time. I love the look of the bridge – great spot for some photos!

    Karen · December 12, 2020 at 2:50 pm

    The photos here are awesome especially with the light low in the sky. You have to climb down to some of the bridges but it’s worth it.

Rowena Li · November 14, 2020 at 9:15 pm

What a beautiful place! New England is the only area in the US that I really haven’t explored much. Looking forward to doing so one day when it’s safe to travel again!

    Karen · December 12, 2020 at 2:51 pm

    I’m biased but New England is really worth an extended visit.

Joanna · November 15, 2020 at 6:39 am

What a lovely hike! It somehow reminded me of the last part of the trek to Machu Picchu, where you have to trek along the rail. The scenery there is different though, more tropical. Does the trail go through the bridges?

    Karen · December 12, 2020 at 2:43 pm

    The trail went beside the bridges. Some of them were still active. Mostly, the river went through the bridges and you could climb down to see them from below.

Jamie · November 15, 2020 at 8:14 am

I grew up in Massachusetts so loved seeing a trail in the Berkshires covered in the article. This was absolutely gorgeous! I felt transported back home, thanks so much for sharing.

    Karen · December 12, 2020 at 2:42 pm

    Always happy to make someone homesick. Massachusetts doesn’t get enough credit as a natural destination.

M.K. Dymock · November 16, 2020 at 8:59 pm

I love hikes to little pieces of history.

    Karen · December 12, 2020 at 2:39 pm

    Me too. The railroad history here is awesome. And the natural history too.

Farrah · November 17, 2020 at 12:29 am

Ooo, I’ve never been here but it’d be cool to get to check out this trail someday! Beautiful photos! <3

    Karen · November 20, 2020 at 9:53 pm

    Yes, this trail is worth doing on any New England trip.

Tara · November 17, 2020 at 10:46 am

Do you live near here, Karen? I loved reading about this cool hike and totally want to plan a trip. I just got sidetracked looking into renting that caboose! My husband comes from a family of masons and I know he would love to check out the Keystone arches.

    Karen · November 20, 2020 at 9:52 pm

    I live about an hour away in the Pelham hills. I hope you do it–it is superb! The masonry on the keystones is so interesting as it’s like an engineer’s magic.

Kristen · November 17, 2020 at 11:26 am

My parents have a home in the Berkshires! I’ll have to check out this hike next time I visit. I don’t think we’ve done this one before. I’ll also send this article to my parents so they can check it out soon!

    Karen · November 20, 2020 at 9:50 pm

    yes, definitely send it to them. It’s such a gorgeous and interesting hike.

Josy A · November 17, 2020 at 2:58 pm

Caboose camping sounds like so much fun! I already love it when old trainlines are made into hiking routes, but finishing off by sleeping in a caboose makes this hike even better!

The keystone arches are beautiful too.

    Karen · November 20, 2020 at 9:49 pm

    I’d get a kick out of the caboose camping too. It’s not open at the moment so I didn’t get to try it.

Francesca · November 18, 2020 at 12:09 pm

Keystone Arch Bridges Trail looks like such a fun trail. I like that it goes through some cool bridge/tunnels and by railroad tracks!

    Karen · November 20, 2020 at 9:48 pm

    Yes, the bridges are fabulous although you’d need to go in the river to go through them. It is possible when the river is low.

Susan · November 18, 2020 at 9:30 pm

The lighting is so pretty in your photos of the arch bridges! What time of year and day were these taken? You’ve definitely inspired me!

    Karen · November 20, 2020 at 9:46 pm

    The photos were taken in early November during the “golden hour”–late afternoon when the light is perfect.

joe olbrych · December 9, 2020 at 12:19 am

i’ve always wanted to visit keystone arches — my grandfather and i made tentative plans to go when i was home this past winter but never made it. next time hopefully!

thanks for sharing all of this great information. i can’t wait to read through more of your posts 🙂

-joe

    Karen · December 12, 2020 at 2:34 pm

    HI Joe,
    I hope you go, you would enjoy it. By the way, I need to say that the realization of my travel blog here had its seed in that Word Press blog you started in the Backyard Wilderness class. It showed me what was possible. So a big thank you.

Carrie · January 3, 2021 at 6:06 pm

This is beautiful — I grew up in New England and always loved hiking and rafting in the Berkshires. I love that there are year-round activity options nearby. That’s perfect for a weekend getaway!

Sharyn · May 13, 2021 at 2:00 am

This looks like such an interesting trail – I like hiking and learning about the history of where I’m hiking at the same time. Thanks.

Rhonda Albom · May 13, 2021 at 3:12 am

The arch bridges are quite impressive. The scenery is spectacular and makes me want to go and check it out.

Anita · May 13, 2021 at 2:09 pm

This is a beautiful place to go hiking and camping for a day or two. Looks like it guarantees you fresh air and quietness for a well deserved break.

Yanitza · May 15, 2021 at 8:00 pm

Wow! What an amazing hike! The Caboose glamping really caught my attention. It would be such an incredible experience1

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