Day Trips With Dogs Massachusetts – Nestled in the beautiful hills of Western Massachusetts, Chester is a hidden gem of natural beauty, rich history, and plenty of outdoor activities. Whether you are a local looking for a new city to explore in Massachusetts or a foreigner like me looking for a day trip, you will find it in Chester, Massachusetts!
I lived in Berkshire for a few years, but when I lived there I stuck to exploring the central, popular towns like Lenox, Stockbridge, Great Barrington, and Pittsfield.
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It wasn’t until I returned to Connecticut that I began exploring the Berkshires-Berkshire Hill suburbs such as Chester, Otis, Becket, and North Adams.
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Located in the southeastern corner of Berkshire County, it’s an ideal day trip away from Connecticut, just an hour’s drive from West Hartford.
Chester is a perfect trip to rural Massachusetts and a place to visit if you are looking for nature, peace and quiet.
Instead of Starbucks and Dunkin’ Donuts, you’ll find family-owned Carm’s Restaurant & Ice Cream. The ladies behind the counter are friendly but busy with locals and visitors passing by. 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 align yourself with the rolling Westfield River that runs 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 find new trails, explore waterfalls and swimming holes, and enjoy a day in the countryside – head to Chester!
Experience one of Chester’s best trails, the Keystone Arches Trail. The entire route runs 4.7 miles round trip, round trip. But you can walk any time and miles, as the whole route runs along the Westfield River and through lush forests, taking you to the beautiful 19th century railway arch.
These stone structures, some up to 70 feet tall, are the first of their kind in the United States. The combination of history, engineering marvels and natural beauty make this a must see on your Chester adventure!
A very easy trail with some elevation changes. Bring the whole family and leashed dog on a historical adventure in Chester!
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In the 18th century, the land that became the Chester-Blandford State Forest was inhabited by European settlers. The towns of Chester and Blandford were founded in 1783 and 1731, respectively. Like many areas in Massachusetts, forest land was used primarily for timber production and agriculture.
Chester-Blandford Forest covers nearly 3,000 acres and has a variety of trails ranging from easy to moderate.
You can take the 1.9 Sanderson Brook Falls Trail which takes you to Sanderson Falls on a mostly wide flat dirt road.
Or you can do the 4.4-mile Sanderson Brook Falls Loop that takes you past the Memorial Trail and then through the gorge that ends at Sanderson Brook Falls. (For more details on this hike, which includes information that dogs need to know, check out the Sanderson Brook Falls hiking guide.)
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Just 10 minutes from Chester you will find Becket Quarry, a property owned by the Trustees and a must stop on your way to Chester.
“Explore the abandoned mine and the remains of operations that once took place here. “There are carved stone pillars with interpretive panels that describe the history of this granite mine and identify artifacts.”
Beginning in the 1860s, the Chester-Hudson Granite Quarry quarried Chester Blue granite, which was considered for tombstones and monuments, but went bankrupt in the late 1940s and abandoned the equipment. In the late 1990s, the Becket Land Trust purchased the property to protect it from development.
Visited on a hot Sunday, I didn’t see as many people here as I would have liked, but we went early in the morning. As I was leaving, I saw more teenagers coming like a day of swimming and listening to music.
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What if the small town has many waterfalls? We have Sanderson Brook Falls, Glendale Falls and now Goldmine Falls. wow! I would make a trip back to this waterfall city just for this.
You can have a front row seat to see Goldmine Falls just over ten miles away. The whole trail is 0.3 miles round trip, but it is rated ‘moderate’ on AllTrails, because you have to navigate some elevation here, as well as rocks and roots.
🚗 How to get to Goldmine Falls: Click for directions to 42.24771, -72.92436 (Note: Parking is on busy Route 20, next to the ramp in front of the trailhead (unfortunately). So, You must park and cross the road carefully, to reach the road. )
Glendale Falls is one of the tallest and longest waterfalls in Massachusetts and you don’t have to walk to see it!
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Another property owned by The Trustees, is just a 100 foot hike to the base of the falls. But I think I like it the most above the falls: several pools of water that are perfect for splashing around on a hot summer day.
A stunning view from the top of the falls as it flows into the Westfield River greets you just meters from the parking lot. This is another must-see stop on today’s trip to Chester, Massachusetts.
Located at 241 Route 20 in downtown Chester, Carm’s Restaurant is open daily from 7:00 a.m. to 5:00 p.m. m. to 2:00 p.m. m. and serves breakfast, lunch and ice cream.
Check out the menu where you can choose breakfast items like omelets, oatmeal, and pancakes, or order a flatbread, wrap, or salad for lunch!
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I bought a cup of Oreo ice cream with sprinkles to go and it was the perfect snack after a morning of adventure.
For a unique combination of adventure and history, visit the Chester Railway Station Museum. Housed in a restored railway station from the 1840s, this museum showcases the region’s rich railway history. Explore the 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 guided tours, adding an educational touch to your adventure.
“As important as the railroad was in Chester’s life, it was far from the only way people lived in the foothills of the Berkshires. Chester was the first place in the United States where amaryl was discovered and the entire milling industry began here.
Stop by Sunny Mountain Farm in Huntington, minutes from Chester, to check out this woman-owned small business that sells homemade soaps, natural soaps, candles, lotions, and even pet products.
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Visit owner Andrea Mengel’s online store here to get an idea of the farm shop and the products sold here.
If walking isn’t your thing, you can still get your heart pumping by kayaking or paddleboarding down the Westfield River. Known for its natural beauty and varying levels of rapids, this river offers a fun challenge for both beginners and experienced kayakers. The River Westfield runs through Chester and offers plenty of entry points to boot!
Scenic Littleville Lake is a 1,567-acre reservoir with a variety of fish including trout, bass, and penguins for those who want to fish.
Be sure to check the Littleville Lake Facebook page for updates on the lake, water levels, and whether the lake is open or closed!
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“The US Army Corps of Engineers welcomes you to Lake Littleville, approximately one mile off Route 112 in Huntington and Chester, Massachusetts. The 1,567-acre park offers visitors many opportunities to enjoy a variety of outdoor recreation activities. The Lake Littleville Reservoir area is open daily from sunrise to sunset.Located in the beautiful Berkshire Hills, hikers and hikers can enjoy a walk along the old wagon trail that runs along both sides of the lake.During the fall foliage season, Littleville Lake and the surrounding area provide scenic views which is nice. Small picnic area available below the dam.”
Do you visit Chester in winter? Take any of the above routes and turn it into a snowshoe adventure! 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 quiet beauty of this small town in winter.
So pack the snacks and load the little ones into the truck. I hope you have a great day in Chester! New Bedford, a small town in southeastern Massachusetts, is a dog-friendly day trip from Rhode Island. It’s an easy drive from Providence, RI to New Bedford, MA, in about 45 minutes. Once you’re in the New Bedford area, there are plenty of dog-friendly activities to do. We couldn’t do everything on my list in one day because we had so much fun and stayed at some places longer than we wanted.
We left and drove through New Bedford to Mattapoisett to hike the Mattapoisett Rail Trail (link). The weather was absolutely gorgeous and the 4.5-mile trail offered views of Buzzards Bay, ponds and marshes, the city pier, and more. It’s really worth the trip to start.
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