Day Trips With Dogs Massachusetts – Nestled in the beautiful hills of western Massachusetts, Chester is a hidden gem with its natural beauty, rich history, and abundance of outdoor activities. Whether you’re a local looking for a new city to explore in Massachusetts or an out-of-state like me looking for a day trip – you’ll find it in Chester, Massachusetts!
I lived in the Berkshires for a few years, but while I lived there I stuck to exploring the central and popular towns like Lenox, Stockbridge, Great Barrington and Pittsfield.
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It wasn’t until I moved back to Connecticut that I began exploring the fringes of the Berkshires—the Berkshire Hill towns of Chester, Otis, Beckett, and North Adams.
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Located in the southeastern tip of Berkshire County, an ideal day trip distance from Connecticut, just an hour’s drive from West Hartford.
If you’re looking for nature, peace and quiet, the perfect road trip through rural Massachusetts, Chester is the place to visit.
Instead of Starbucks and Dunkin’ Donuts, you’ll find Carm’s Restaurant and Ice Cream, a family-owned business. The women behind the counter are friendly but busy with passing residents and visitors. You may have to wait 10 minutes or more for your turn at the counter, but it’s time to slow down.
Adapt to the city and sync with the gentle Westfield River that flows through it – it’s time for adventure!
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So if you are looking for the perfect day trip to Massachusetts; A place to take new walks, explore waterfalls and swim and enjoy a day out in the countryside – head to Chester!
Experience one of Chester’s iconic trails, the Keystone Arches Trail. The entire route there and back is 7.5 km. But you can walk for miles along the Westfield River and through lush woodland, taking you to the impressive 19th-century railway arches.
These rock formations, some of which are 230 feet tall, are the first of their kind in America. The combination of history, engineering marvels and natural beauty makes it a must-do on your Chester adventure!
A very easy route with minor elevation changes, take the whole family and dogs on this historic Chester adventure!
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In the 18th century, European settlers settled the land that makes up the Chester-Blandford State Forest. The towns of Chester and Blandford were incorporated in 1783 and 1731 respectively. Like many areas of Massachusetts, the forest was used primarily for timber production and agriculture.
Chester-Blandford Forest covers around 3,000 hectares and has a variety of trails ranging from easy to intermediate.
You can also take the 1.9 Sanderson Brook Falls Trail, which takes you to Sanderson Falls on a mostly wide, flat gravel path.
Or you can do the 4.5-mile Sanderson Brook Falls Loop, which takes you to a scenic overlook on the Memorial Trail and then through the gorge ending at Sanderson Brook Falls. (If you want more details on this hike, including some things dogs should know, check out my Sanderson Brook Falls hiking guide.)
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Just 10 minutes outside of Chester you’ll find Beckett Quarry, a property owned by the Trustees and a must stop on your trip to Chester.
“Explore the remains of an abandoned quarry and operation that once took place here, with stone pillars carved with interpretive plaques detailing the history of this granite quarry and identifying artifacts.
The Chester-Hudson Granite Quarry opened in the 1860s and quarried Chester Blue granite, prized for headstones and monuments, but abandoned equipment and went bankrupt in the late 1940s. In the late 1990s, the Beckett Land Trust purchased the property to protect it from development.
When I visited on a warm summer Sunday, there weren’t as many people as I expected, but we went early in the morning. When I went out, I saw more teenagers coming to swim and listen to music.
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How can a small town have so many waterfalls?! We have Sanderson Brook Falls, Glendale Falls and now Gold Mine Falls. Awesome! This is why I keep coming back to this waterfall town.
You can have a front row seat to Goldmine Falls just a tenth of a mile away. The entire trail is 0.5 miles round-trip, but is rated “moderate” on the AllTrails because it involves some elevation as well as navigating rocks and roots.
🚗 Go to Goldmine Falls: For directions, click 42.24771, -72.92436 (Note: The parking lot at the turn opposite the trail entrance is on busy Route 20 (unfortunately)) so you’ll need to park and ‘walk the road’ to get to the track.)
Glendale Falls is one of the tallest and longest flowing waterfalls in Massachusetts and you only have to hike to see it!
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Another property owned by the trustees, it is approximately a 30 meter walk to the base of the falls. But I think I liked the top of the falls the most: several water holes, perfect for wading through on a hot summer day.
A dramatic view over the falls flowing into the Westfield River greets you just yards from the parking lot. This is another must stop on this day trip to Chester, Massachusetts.
Carms Restaurant, located at 241 Route 20 in the heart of Chester, is open daily from 7am to 2pm for breakfast, lunch and ice cream!
Check out the menu where you can choose your choice of breakfast items such as omelets, oatmeal and pancakes, or pick up a flatbread, wrap or salad for lunch!
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I got a cup of Oreo ice cream with sprinkles and it was the perfect snack after a morning adventure.
Visit the Chester Railway Station Museum for a unique blend of adventure and history. Housed in a restored 1840s station, the museum showcases the region’s rich railway history. Explore exhibits, walk old tracks, and imagine the days when steam engines roared through the hills of western Massachusetts. The museum also offers special events and tours, giving your adventure an educational twist.
As big a deal as the railroad played in Chester’s life, it was far from the only way people lived in this foothills of the Berkshires. Chester was the first place in America where emery was discovered and the grinding industry began here.
Stop by Sunny Mountain Farm in Huntington minutes outside of Chester for this small, woman-owned business that offers homemade and natural soaps, candles, lotions and pet products!
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View owner Andrea Mengel’s online store here to get an impression of the farm shop and the products sold here.
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 various levels of rapids, this river offers an exciting challenge to beginners and experienced kayakers alike. The River Westfield runs through Chester and offers plenty of access points to get started!
Scenic Littleville Lake is a 1,567-acre lake with a variety of fish including trout, bass and pike for those looking for fish.
Be sure to check the Littleville Lake Facebook page for lake updates, water levels, and when the lake is open or closed!
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“The US Army Corps of Engineers leads you off Rt.112 to Massachusetts’ 1,567-acre park with many opportunities to enjoy a variety of outdoor recreational activities. The area is open daily from sunrise to sunset. A small picnic area is available below the dam with views of many beautiful landscapes.
Visiting Chester in winter? Take one of the above routes and make it a snow adventure! Chester-Blandford State Forest and trails around Littleville Lake are perfect for cross-country skiing or snowshoeing. Glide through the snow-covered landscape, breathe in the fresh winter air and enjoy the quiet beauty of this small town in winter.
So pack some snacks and load the puppies into the truck. I hope you had a great day in Chester! From east to west, the United States is rich with active, scenic, and lively dog-friendly vacations. From gondola rides to visits to local breweries, you and your child are invited to explore the 42 destinations below without limits!
Our vans are perfect for pet owners looking to take the whole family on their next adventure. There’s plenty of room for passengers, puppies and everyone else’s travel needs.
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National parks are great places to hike with dogs, and Acadia National Park is one of the best. There are more than 100 miles of trails to explore, and a free, dog-friendly bus takes riders around the park and island.
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