5.0
(1)
21
hikers
5
hikes
Hiking in Middlefield State Forest, Massachusetts, offers varied terrain characterized by lush greenery, rolling hills, and babbling brooks. The landscape features towering hardwood trees and diverse wildflowers, with elevations generally between 1,550 and 1,850 feet. Hikers can explore steep slopes ascending from Tracy Pond, as well as flatter areas to the east of the water. The forest borders the Tracy Pond Wildlife Management Area, providing access to an expansive natural setting.
Last updated: July 8, 2026
5.0
(1)
14
hikers
7.25km
01:59
120m
120m
The Keystone Arch Bridges Trail offers a captivating journey through remote woods, where the Westfield River carves its way through the landscape. You'll hike along dirt paths, navigating occasional rocks and roots, with the highlight being the series of impressive 19th-century stone arch railroad bridges that punctuate the route. The scenery shifts between dense forest and open river views, creating a dynamic and engaging experience for hikers of all ages.
This easy 4.5-mile (7.3 km) hike, with a modest 388 feet (118 metres) of elevation gain, typically takes just under 2 hours to complete. It's an ideal choice for families or those seeking a historically rich and scenic outing without a strenuous climb. The trail is especially popular in autumn for its vibrant foliage, but it offers a pleasant walk year-round. Allow extra time to explore the areas around the bridges and enjoy the river access points.
What truly sets this trail apart are the magnificent stone arch bridges, built between 1833 and 1841 without mortar or steel, an incredible feat of engineering for their time. These structures are among the oldest railroad bridges of their kind in the United States, making the route a living museum of railway history. The trail also follows a federally designated Wild & Scenic River, adding to its natural appeal and making it a unique blend of human ingenuity and natural beauty in the Berkshires.
1.20km
00:21
50m
0m
Hike an easy 0.7-mile section of the Appalachian Trail to Warner Hill for expansive views of Mt. Greylock and the Housatonic Valley.

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2
hikers
4.64km
01:13
40m
40m
Hike the easy 2.9-mile Old Mill Trail in Dalton, Massachusetts, exploring river views and historical mill ruins.
3
hikers
14.2km
04:02
240m
460m
Embark on a moderate hike along the Appalachian Trail from Washington to Dalton, covering 8.8 miles (14.2 km) with an elevation gain of 771 feet (235 metres). This section offers a classic A.T. experience through varied terrain, featuring rocky and rooted singletrack paths that wind through a very pretty forest. You will enjoy gentle climbs to wooded summits like Warner Hill, where you can catch views of Mount Greylock, and the route typically takes around 4 hours and 2 minutes to complete.
When planning your visit, be aware that while the trail is generally moderate, you might encounter slippery rocks and roots, especially after rain. Parking is usually available at the trailheads, but it's always wise to check local conditions before you go. As you approach Dalton, the trail transitions into a road walk, leading you towards amenities in this accessible A.T. Community.
This segment of the Appalachian Trail is known for its abundant wildflowers in season and frequent deer sightings. You'll also pass the remains of extensive beaver ponds, adding to the natural charm of the route. Keep an eye out for a side trail that leads to the Kay Wood Shelter, offering a glimpse into the trail's support system.
4.0
(1)
4
hikers
26.4km
07:16
430m
430m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Popular around Middlefield State Forest
This is the site of the ruins of the Plunkett Brothers Mill. The mill was working until 1930 and produced a range of textiles, including blankets, shirts and skirts. The mill was run on energy created by the Housatonic River. Once the mill shut down, it was abandoned and over the 90 years, nature has slowly reclaimed the area.
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The Old Mill Trail is a beautiful path that runs along the Housatonic River from Dalton to Hinsdale. The trail passes through several historic sites, including an old dam and the Plunkett Brothers mill.
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Warner Hill is one of the many peaks on the Appalachian trail as it pass through Massachusetts. The path to the top passes through dense woodland, but once you get to the top, there is a great view onto the Berkshire Range
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The Appalachian Trail passes nearby Pittsfield. you cross the path on this road. It goes south to the October mountain state forest, and north to Dalton. Maybe an idea for a future hike?
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Finerty Pond is one of the larger lakes in the October Mountain State Forest. There is a direct link to the lake from the Tyne Road car park.
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Deep gorges, high mountains, shiny ponds and wild animals – October Mountain State Forest is a divers natural area and the largest state forest in Massachusetts. You will find hiking trails for just strolling or ambitious adventures as well as a campground. It is also a section of the Appalachian Trail.
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Komoot currently lists 4 hiking routes in Middlefield State Forest, offering a variety of experiences for different skill levels.
The terrain is characterized by lush greenery, rolling hills, and babbling brooks. You'll find a mix of towering hardwood trees and diverse wildflowers. The landscape is notably hilly, with steep slopes ascending from Tracy Pond, though some flatter areas are present to the east of the water.
Yes, Middlefield State Forest offers several easy trails. For instance, the Old Mill Trail — Dalton is an easy 2.9-mile path through woodland with minimal elevation gain, perfect for a relaxed walk.
Hikers can enjoy diverse natural features including Tracy Pond, which is home to various warm-water fish species, and a small brook that feeds into it. The dense forest is teeming with wildlife such as white-tailed deer and black bears, with waterfowl around Tracy Pond. You'll also encounter towering hardwood trees and vibrant wildflowers.
The area is highly rated by the komoot community, with an average score of 4.5 stars. Hikers often praise the tranquil retreat, scenic beauty, and the diverse natural features that make for an invigorating outdoor experience.
Yes, for those seeking a more challenging experience, the Finerty Pond – October Mountain State Forest loop from Becket is a difficult 16.4-mile trail that leads through dense forest and around Finerty Pond, typically taking over 7 hours to complete.
Generally, dogs are welcome on trails in Massachusetts state forests, but it's always recommended to keep them on a leash and clean up after them. Check local signage for any specific restrictions on individual trails within Middlefield State Forest.
Yes, the Keystone Arch Bridge loop from Keystone Arch Bridge "E" is a popular circular route, offering an easy 4.0-mile path through varied forest.
Much of the forest rests between 1,550 and 1,850 feet in elevation, offering varied ascents and descents, particularly around Tracy Pond.
Yes, the forest offers trails suitable for various fitness and skill levels, including easy hikes like the Old Mill Trail — Dalton, which are great for families looking for a relaxed walk through nature.
The dense forest is home to various wildlife, including white-tailed deer and black bears. Around Tracy Pond, you might also spot various waterfowl.
Many trails offer scenic beauty with lush greenery, rolling hills, and babbling brooks. The area around Tracy Pond and the routes through the towering hardwood trees are particularly picturesque.


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