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Routes
Hiking trails & Routes
United States
Massachusetts
Essex County
Gloucester

Dogtown Woods Circular

Moderate

3.3

(11)

57

hikers

Dogtown Woods Circular

03:30

13.4km

100m

Hiking

Embark on the Dogtown Woods Circular, a moderate hike spanning 8.3 miles (13.4 km) with an elevation gain of 317 feet (97 metres), typically completed in about 3 hours and 30 minutes. You will wander through dense woodlands, encountering dramatic glacial boulders and winding trails that pass natural water features like the Goose Cove Reservoir. Keep an eye out for the unique Babson Boulders, which are inscribed with inspirational mottoes, adding a distinctive artistic and historical touch to your journey.

Before you head out, be aware that the trails in Dogtown Woods are not always clearly marked, so carrying a map is highly recommended for navigation. The terrain can be rugged in certain sections, requiring you to navigate over large boulders, so make sure you wear appropriate footwear for a comfortable experience. Parking is generally available at the trailheads, making access straightforward for your visit.

This route takes you through the historic Dogtown Common, offering a fascinating glimpse into a 17th-century colonial settlement. As you hike, you will discover remnants of the past, including old cellar holes and forgotten rock walls that tell stories of the area's early inhabitants. The blend of natural beauty and rich history makes this trail a notable experience in Gloucester, Massachusetts.

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

Get Directions

1

2.06 km

James Babson Museum

Highlight • Historical Site

James Babson Museum is a small, one room museum in a historic building dating back to the late 1700s. Opened by Roger Babson in the 1930s, he created a one room museum filled with an extensive collection of tools and artifacts from the area. Currently on display are various antique tools covering over three centuries for trades such as blacksmithing, coopering, and farming that would have been used on Cape Ann. Admission to this small, local museum is free so there is no reason why not to make a quick stop here before or after exploring the Babson Woods.

Tip by

6.65 km

Swett Woodlot

Nature Reserve

3

8.34 km

Goose Cove Reservoir is an attractive freshwater pond and is one of the main sources of water for Gloucester. From this spot on the north end of Goose Cove Reservoir, on top of an earthen dam, you get great views across the clear water; these views are exceptionally nice in the fall when the changing leaves are reflected on the ponds surface. There is a great hiking loop around the entirety of the pond; it is a popular trail for locals and visitors alike. There are numerous trails off of the semi-paved loop leading into the Dogtown Woods.

Tip by

8.84 km

Goose Cove Reservoir Watershed

Nature Reserve

5

9.33 km

Goose Cove Reservoir

Highlight • Lake

Technically the loop around this reservoir is paved, but it's in rough enough shape that a mountain bike isn't a bad choice at all.

Tip by

6

10.1 km

Dogtown Commons

Highlight • Historical Site

Although this area is perhaps better known for the Babson Boulders and their quirky phrases, Dogtown's history extends far past the Great Depression. Dogtown was originally known as the Common Settlement when it was settled in 1693. Within a few decades, there were about 60 to 80 homes in Dogtown, and by the mid-1700s through the American Revolution, there were as many as 100 families in Dogtown. Although none of these early homes remain, you can still make out cellar holes from this period in this area. Babson mapped and numbered these holes in the 1930s with caved rocks that you can see today.

Tip by

B

13.4 km

End point

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Way Types & Surfaces

Way Types

6.22 km

4.88 km

2.20 km

< 100 m

Surfaces

9.10 km

2.39 km

1.41 km

260 m

< 100 m

< 100 m

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Elevation

Elevation

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Sunday 10 May

19°C

9°C

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This route was planned by komoot.

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Frequently Asked Questions

How long does it take to hike the Dogtown Woods Circular?

The entire 13.4 km (8.3 mile) circular route typically takes around 3 hours and 30 minutes to complete. This duration can vary based on your pace and how much time you spend exploring the historical sites and glacial boulders.

Is the Dogtown Woods Circular trail suitable for beginners?

While the overall route is rated as moderate, Dogtown Woods offers a network of trails with varying difficulties. Some sections are easy walks, but others require navigating over large boulders and can be rugged with rocks and roots. Beginners should be prepared for some challenging terrain, and a map is highly recommended.

What is the terrain like on the Dogtown Woods Circular trail?

The terrain is primarily dense woodlands with dramatic glacial boulders. You'll hike through forested areas, past natural water features like Goose Cove Reservoir (North Dam) and Goose Cove Reservoir. Expect rugged sections, old cellar holes, overgrown apple orchards, and forgotten rock walls, especially around Dogtown Commons.

What historical and natural features can I see along the route?

This trail is rich in history and unique natural formations. You can explore remnants of a 17th-century colonial settlement, including cellar holes and old roads. A significant attraction is the 'Babson Boulders,' large glacial rocks carved with inspirational mottoes during the Great Depression. You'll also pass by the James Babson Museum and enjoy tranquil ponds and captivating rock formations.

Is the Dogtown Woods Circular trail dog-friendly?

Yes, the Dogtown Woods trails are generally dog-friendly. However, given the rugged terrain, including large boulders and rocky sections, ensure your dog is capable of handling the hike. Always keep your dog on a leash and practice Leave No Trace principles.

What is the best time of year to hike the Dogtown Woods Circular?

Dogtown Woods offers a unique experience in every season. Spring brings new growth, summer provides lush canopies, and fall showcases vibrant foliage. Winter hiking is also possible, but be prepared for potentially icy or snowy conditions, especially on rocky sections. Always check local weather conditions before heading out.

Where can I park for the Dogtown Woods Circular trail?

Specific parking information for the Dogtown Woods Circular trailhead is not detailed, but Dogtown Common has several access points with parking areas. It's advisable to check a local map or online resources for the most convenient and designated parking spots near your chosen starting point.

Are there any entrance fees or permits required for Dogtown Common?

No, there are typically no entrance fees or permits required to access Dogtown Common or its trails, including the Dogtown Woods Circular. It is open to the public for recreation.

Does the Dogtown Woods Circular trail intersect with other paths?

Yes, the route utilizes sections of several other trails within Dogtown Common. You will hike along parts of Old Rockport Road, Tarr Trail, Dinosaur, Common Road, and Dinosaur Bail, among others, as you complete the circular route.

What should I bring for a hike on this trail?

Given the varied and sometimes rugged terrain, we recommend sturdy hiking boots, plenty of water, and snacks. A physical map or a reliable GPS app is highly recommended, as trails are not always well-marked. Don't forget your camera to capture the unique historical sites and natural beauty!

Are there any specific tips for navigating the Dogtown Woods Circular trail?

Due to the extensive network of trails and sometimes unclear markings, carrying a detailed map or using a GPS device is crucial for navigation. Be prepared for sections that require stepping over large boulders and roots. QR codes on signage can provide additional historical context, so keep an eye out for them.

Is the Dogtown Woods Circular suitable for families with children?

While the full circular route is moderate, Dogtown Woods offers many shorter, easier sections that are great for families. For example, the 2.0-mile Goose Cove Reservoir loop is generally easy. If hiking with children, consider shorter segments and be aware that some parts of the main circular trail are rugged and require careful footing.

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