Adventurous Day Trip to Chester, Massachusetts; Walks & Waterfalls

Nestled in the picturesque hills of Western Massachusetts, Chester is a hidden gem with its natural beauty, rich history, and a plethora of outdoor activities. Whether you’re a local looking for a new town to explore in Massachusetts or an out-of-stater like me looking for a day trip – you’ll find it in Chester, Massachusetts!

I lived in the Berkshires for several years yet while living there I stuck to exploring the central and most popular towns like Lenox, Stockbridge, Great Barrington, and Pittsfield.

It wasn’t until I moved back to Connecticut that I started exploring the edges of the Berkshires—Berkshire Hill towns like Chester, Otis, Becket, and North Adams.

Located on the southeastern edge of Berkshire County, it’s an ideal day trip distance from Connecticut at just an hour’s drive from West Hartford.

Chester is the perfect Massachusetts country road trip and is a place to visit if you’re looking for nature, peace, and quiet.

Instead of Starbucks and Dunkin’ Donuts, you’ll find family-owned Carm’s Restaurant & Ice Cream. The women behind the counter are friendly but busy with locals and visitors passing through. You might have to wait 10 or more minutes for your turn at the counter but this is time to SLOW down.

Adjust to the town and get in sync with the rolling Westfield River that runs through it – it’s time for an adventure!

So if you’re looking for the perfect Massachusetts day trip; a place to find new hikes, explore waterfalls and swimming holes, and enjoy a day out in the country – head to Chester!

Adventurous Day Trip Itinerary for Chester, Massachusetts

1. Hike the Keystone Arches Trail

Experience one of Chester’s most iconic trails, the Keystone Arches Trail. The full trail travels 4.7 miles round trip, out and back. But you can walk for any amount of time and miles as the whole trail runs all along the Westfield River and through lush forests, leading you to the stunning 19th-century railroad arches.

These stone structures, some reaching up to 70 feet high, were the first of their kind in America. The combination of history, engineering marvels, and natural beauty makes this a must-do stop for your Chester adventure!

A very easy trail with little elevation changes, bring the whole family and leashed dogs on this historic Chester adventure!

🚗 Getting to Keystone Arches Trail: Click for directions to 42.31152, -72.99265

2. Hike and explore Chester-Blandford State Forest

In the 18th century, the land that makes up Chester-Blandford State Forest was settled by European colonists. The towns of Chester and Blandford were established in 1783 and 1731, respectively. Like many areas in Massachusetts, the forested land was primarily used for timber production and farming.”

The Chester-Blandford Forest forest encompasses almost 3,000 acres and has a variety of trails that range from easy to moderate.

Sanderson Brook Falls is just one of many scenic waterfalls in the Berkshires.

You can take the 1.9 Sanderson Brook Falls Trail which leads you on a mainly wide flat gravel path to Sanderson Falls.

Or you can do the 4.4-mile Sanderson Brook Falls Loop which takes you up to sweeping vistas on the Memorial Trail and then down along a gorge that ends at Sanderson Brook Falls waterfall. (If you want more details on this hike which has some need-to-know info for dogs, check out my Sanderson Brook Falls Hike Guide.)

🚗 Getting to Sanderson Brook Falls: Click here for directions to 42.25572, -72.947

3. Visit Becket Quarry

At just 10 minutes outside of Chester you’ll find Becket Quarry, a Trustees-owned property, and it’s a must-stop for your trip to Chester.

“Explore the abandoned quarry and remnants of the operation that once functioned here. There are carved stone pillars topped with interpretive panels that detail the history of this granite quarry and identify artifacts.”

Beginning in the 1860s, the Chester-Hudson Granite Quarry extracted Chester Blue granite, prized for gravestones and monuments, but became insolvent by the late 1940s, leaving equipment abandoned. In the late 1990s, the Becket Land Trust purchased the property to protect it from development.

Visiting on a warm summer Sunday, I didn’t see as many people here as I would expect but we went earlier in the morning. On the way out I saw more teenagers arriving for what looked like a day of swimming and listening to music.

Note: swimming and cliff diving is not allowed

🚗 Getting to Becket Quarry: Click for directions via Google Maps

5. Short walk to Goldmine Falls

How does one little town have so many waterfalls?! We’ve got Sanderson Brook Falls, Glendale Falls, and now Goldmine Falls. Wow! I would make the trip back to this waterfall town for these alone.

You can have a front row seat to Goldmine Falls for just a little more than one tenth of a mile. The whole trail is 0.3 miles round trip but rated ‘moderate’ on AllTrails as you will have to navigate a little elevation here as well as rocks and roots.

🚗 Getting to Goldmine Falls: Click for directions to 42.24771, -72.92436 (Note: Parking is on the busy Route 20 along a pull-off across from the trail entrance (unfortunately.) So you have to park and carefully cross the street to get to the trail.)

6. Glendale Falls

Glendale Falls is one of the tallest and longest waterfall runs in Massachusetts and you barely have to hike to see it!

Another property owned by The Trustees, it’s just about a 100-foot walk to the base of the waterfall. But it was at the top of the waterfall that I think I loved the most – several pools of water perfect for wading in on a summer day.

The dramatic view from the top of the waterfall as it flows into the Westfield River greets you just feet from the parking lot. This is another must-stop on this Chester, Massachusetts day trip.

🚗 Getting to Glendale Falls: Click for directions to 42.34958, -72.96705

7. Stop by Carm’s Restaurant & Coffee Shop

Located at 241 Route 20 right in the Center of Chester, Carm’s Restaurant is open every day from 7am-2pm serving breakfast, lunch, and ice cream!

Check out the menu where you can take your pick of breakfast items like omelettes, oatmeal and pancakes or get a flatbread, wrap, or salad for lunch!

I got a cup of Oreo ice cream with sprinkles to go and it was the perfect snack after a morning of adventures.

🚗 Getting to Carm’s Restaurant: Click for directions via Google Maps

8. Attend the Chester Railway Station & Museum

For a unique blend of adventure and history, visit the Chester Railway Station Museum. Housed in a restored 1840s train station, the museum showcases the rich railroad history of the area. Explore the exhibits, walk along the old tracks, and imagine the days when steam engines roared through the hills of Western Massachusetts. The museum also offers special events and guided tours, adding an educational twist to your adventure.

“As big a part as the railroad was in Chester life, it was far from the only way people earned a living in these foothills of the Berkshires. Chester was the first place in America where emery was discovered and the entire grinding industry began here.”

🚗 Getting to Chester Railway: Click for directions via Google Maps

9. Stop at Sunny Mountain Farm Shop

Stop by Sunny Mountain Farm in Huntington, minutes outside of Chester, for this woman-owned small business for homemade and natural soaps, candles, lotions, and even pet products!

Check out owner Andrea Mengel’s online store here to get a sense of the farm shop and products sold here.

🚗 Getting to Sunny Mountain Farm: Click for directions via Google Maps (413)250-0411

4. Kayak the Westfield River

If hiking isn’t your thing you can still get your heart pumping with a kayaking or paddling trip down the Westfield River. Known for its scenic beauty and varying levels of rapids, the river provides an exciting challenge for new novice and experienced kayakers. The Westfield River flows through Chester, offering numerous entry points for you to launch!

sign of westfield river in chester massachusetts

10. Visit Littleville Lake

Scenic Littleville Lake is a1,567-acre reservoir is stocked with a variety of fish, including trout, bass, and pickerel for those looking to fish.

Be sure to check the Littleville Lake Facebook page about lake updates, water levels, and if the lake is open or closed!

“The U.S. Army Corps of Engineers welcomes you to Littleville Lake about one mile off Rt.112 in Huntington and Chester, Mass. The 1,567 acre park offers visitors many opportunities to enjoy a variety of outdoor recreation activities. The Littleville Lake Reservoir Area is open daily from sunrise to sunset. Situated in the scenic Berkshire Hills, hikers and sightseers can enjoy wandering along the old cart roads that run on both sides of the lake. During the fall foliage season, Littleville Lake and nearby areas provide leaf peepers with many scenic vistas. A small picnic area available just below the dam.”

Winter Adventures: Snowshoeing and Cross-Country Skiing

Visiting Chester in the winter? Take any of the above trails mentioned and turn them into a snowshoe adventure! The Chester-Blandford State Forest and the trails around Littleville Lake are perfect for cross-country skiing or snowshoeing. Glide through the snow-covered landscape, breathe in the crisp winter air, and enjoy the serene beauty of this small town in winter.

I hope you enjoyed this special day Massachusetts day trip to the quaint town of Chester!

There are obviously numerous hikes to choose from and waterfalls to visit in this small Berkshire town.

So pack some snacks and load the pups in the truck. I hope you have a great day in Chester!

Comment below with another favorite adventurous day trip town in Massachusetts! ⬇️⬇️

Looking for more hikes in the Berkshires? Check out my post – 13 Hikes in the Berkshires.

woman hiking with dog in the Berkshires

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  1. The Berkshires has been on my list for years! I was supposed to go there a couple years ago, but then I got a kidney stone so the plans had to change. But, I would love to visit Chester, it looks like such a great area to explore!

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