4.6
(717)
5,201
hikers
438
hikes
Hiking around Upton, Massachusetts, features diverse natural landscapes, including extensive forests of oak, maple, and pine, alongside cold water streams, wetlands, and vernal pools. The region is characterized by unique glacial formations, such as large boulder fields and glacial erratics. Varied topography includes the expansive Upton State Forest and hills offering scenic vistas. Many trails also incorporate historical elements, including stone walls and structures from the Civilian Conservation Corps.
Last updated: June 22, 2026
5.0
(1)
4
hikers
16.4km
04:22
180m
180m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
6
hikers
6.91km
01:49
60m
60m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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8
hikers
4.48km
01:09
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(2)
7
hikers
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
4.0
(1)
5
hikers
4.81km
01:13
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Disused railway line, perfectly flat and straight.
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Blewbury is a gorgeous little village located at the foothills of the Berkshire Downs. The village is surrounded by farmland and overlooked by an iron-age hillfort. It's nearby to many beautiful walks, including the Ridgeway, Britain's oldest road!
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Still closed to cars as of 14/04/22
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Asphalt road to the farm, with big views over Didcot & beyond
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Bridleway over the A34 - connecting up to Harwell Labs
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In Mar 2022, still closed for road users - blocked off with concrete bollards.
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As of April 2021 the road is temporarily shut to traffic but open to cycles
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Upton offers a wide variety of hiking opportunities, with over 400 routes recorded on komoot. These trails range from easy strolls to more challenging paths, catering to different experience levels.
Yes, Upton has numerous easy trails perfect for beginners and families. Many conservation areas, such as Heritage Park, offer gentle paths. The Hike Upton Challenge also lists several accessible options, including trails at Goss Pond and Snow Family Conservation Area.
Upton's natural areas are incredibly diverse, featuring extensive forests dominated by oaks, maples, and pines, along with cold water streams, wetlands, and vernal pools. You'll also encounter unique glacial formations, such as the boulder fields on Peppercorn Hill, and tranquil waterways like Warren Brook and the West River.
Many trails in Upton wind through areas rich in history. You can find historic stone walls and cellar holes, offering glimpses into the region's past. Upton State Forest also contains structures built by the Civilian Conservation Corps (CCC) during the Great Depression. A notable landmark is the "Upton Cave" or "Upton Chamber" in Heritage Park, one of the largest and most perfectly built stone chambers in the Northeast.
Many of Upton's conservation lands and state forests are dog-friendly, but it's always best to check specific regulations for each area. Generally, dogs are welcome on trails if kept on a leash and owners practice responsible pet waste removal. Areas like Upton State Forest and Peppercorn Hill are popular choices for walks with canine companions.
Yes, Upton offers several circular routes, which are great for exploring without retracing your steps. For example, the Whitehall State Park β Whitehall Reservoir loop in Upton State Forest is a popular 8.5-mile moderate circular trail. Peppercorn Hill Conservation Area also features a favored 3.1-mile loop from its Camp St Site.
The komoot community highly rates hiking in Upton, with an average score of 4.6 stars from over 600 reviews. Hikers often praise the diverse natural landscapes, the tranquility of the woodlands, and the well-maintained trails that offer a mix of easy and moderate options.
For detailed trail maps of Upton's various conservation lands, you can visit the official town website. They provide resources to help you plan your hikes and explore areas like Peppercorn Hill, Warren Brook, and Heritage Park. You can find more information at uptonma.gov.
While Upton is known for its extensive network of shorter trails, you can combine routes within larger areas like Upton State Forest to create longer hikes. The forest itself spans 2,660 acres, offering ample space for extended exploration. The Whitehall State Park β Whitehall Reservoir loop is a good example of a longer, moderate route at 8.5 miles.
Keep an eye out for the unique glacial formations, particularly the impressive jumble of boulders on the western slope of Peppercorn Hill. You'll also encounter diverse ecosystems, from dense forests to wetlands and vernal pools, which are particularly vibrant in spring. The tranquil waters of Warren Brook and the West River also add to the scenic beauty.
Yes, Upton encourages exploration through its "Hike Upton Challenge." This program invites residents and visitors to complete any 6 out of 10 designated hikes across various conservation areas to earn a pin or patch, promoting engagement with the town's natural beauty.
Upton offers enjoyable hiking experiences year-round. Spring brings blooming wildflowers and active vernal pools, while summer provides lush greenery. Fall is particularly scenic with vibrant foliage. Winter hiking is also popular, especially in areas like Upton State Forest and Warren Brook Watershed Conservation Area, which are suitable for cross-country skiing.


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