Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Hikes
United States
Massachusetts
Essex County

Gloucester

Easy hikes and walks around Gloucester

4.5

(28)

356

hikers

53

hikes

Easy hiking trails around Gloucester offer a diverse landscape for outdoor exploration. The region features a mix of rolling hills, woodlands, and riverside paths, providing varied terrain for hikers. Notable natural features include the Cotswold escarpment, the River Severn, and numerous country parks. This varied topography ensures a range of easy routes suitable for different preferences.

Best easy hiking trails in Gloucester

  • The most popular easy hiking route is Babson Boulder and Dogtown Road Loop, a 1.9 miles (3.0 km) trail that takes 48 minutes to complete. This route explores a historic forested area with unique rock formations.
  • Another top favourite among local hikers is Magnolia Woods and Rafes Chasm Trail Loop, an easy 2.4 miles (3.9 km) path. This trail offers coastal views and woodland scenery.
  • Local hikers also love the Stage Fort Trail, a 2.6 miles (4.3 km) trail leading through parkland and along the waterfront, often completed in about 1 hour 8 minutes.
  • Hiking around Gloucester is defined by its varied terrain, including coastal paths, forested hills, and riverine landscapes. The network offers options for different ability levels, with many easy hiking trails available.
  • The routes in Gloucester are highly rated by the komoot community with an average score of 4.5 stars from over 10 reviews. More than 180 hikers have used komoot to explore Gloucester's varied terrain.

Last updated: April 26, 2026

3.0

(1)

4

hikers

#1.

Babson Boulder and Dogtown Road Loop

2.99km

00:48

30m

40m

Embark on an easy 1.9-mile (3.0 km) hike through a historic woodland on the Babson Boulder and Dogtown Road Loop. This route offers a wild feel, guiding you over varied terrain that includes both paved sections and rocky, rooted paths. You will encounter dramatic glacial boulders, such as the famous Whale's Jaw, and the unique Babson Boulders, which are carved with inspirational messages. With an elevation gain of 113 feet (34 metres), this loop takes approximately 48 minutes to complete, making it a perfect short outing.

Parking is generally available at the trailheads that access Dogtown Conservation Land, making your start straightforward. Before you set out, remember to check local weather conditions, as some parts of the trail can become rocky and slippery after rain. While the Babson Boulder and Dogtown Road Loop is rated easy, be aware that certain paths, like Nellie's Trail, feature numerous rocks and roots. Plan your visit during dry conditions for the most comfortable experience.

This area is rich with history, preserving remnants of a 17th-century settlement. As you hike, you will discover intriguing historical artifacts like old cellar holes and stone walls scattered throughout the landscape. The trail offers a unique blend of natural beauty and human history, providing insight into the past of Dogtown Commons. It stands out as a place where you can connect with both nature and the stories of early inhabitants.

Navigate with device

Send to Phone

Save

Easy

Embark on an easy hike through the serene Magnolia Woods and Rafes Chasm Trail Loop, a 2.4 miles (3.9 km) route that offers a gentle escape into nature. You will experience a tranquil walk through the wooded landscape, where the path remains generally flat and accessible. The trail leads you towards the coast, culminating in spectacular views from the rocky cliffs at Rafe's Chasm. Here, crashing waves and tide pools create a mesmerizing sight, and you can even spot Norman's Woe rock and Kettle Island in the distance. This pleasant journey involves a modest 114 feet (35 metres) of elevation gain and typically takes about 1 hour and 2 minutes to complete.

When planning your visit, be aware that while the woodland sections are straightforward, reaching Rafe's Chasm involves navigating over rocks. These rocks can become slippery from water, ice, or sea life, depending on the time of year. For this reason, we recommend wearing good hiking footwear to ensure a secure footing on the rocky terrain. Trekking poles can also be helpful for added stability, especially if you are concerned about uneven surfaces. Due to the potentially slippery and irregular ground near the chasm, this specific part of the route might be less suitable if you have mobility challenges.

The Magnolia Woods and Rafes Chasm Trail Loop is nestled within the Magnolia Woods Recreational Area, offering a diverse experience that transitions from peaceful forest to dramatic coastal views. The highlight at Rafe's Chasm is a unique natural formation where the ocean's power is on full display, creating a dynamic and ever-changing seascape. This trail stands out for its accessibility combined with the striking contrast between its wooded beginning and its rugged, scenic coastline. It provides a perfect opportunity to enjoy both forest tranquility and the raw beauty of the sea in one compact outing.

Easy
guide_signup
Let us show you the way with the komoot mobile app
With aΒ free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

3

hikers

4.25km

01:08

50m

50m

The Stage Fort Trail offers an easy hiking experience, covering 2.6 miles (4.3 km) with a gentle elevation gain of 148 feet (45 metres). You can expect to complete this route in about 1 hour and 7 minutes, enjoying a diverse journey through both woodland and coastal landscapes. As you hike, you will pass large rock formations and discover panoramic ocean views, especially from the designated Viewpoint overlooking the Atlantic Ocean and Gloucester Harbor.

Planning your visit to Stage Fort Park is straightforward, as the trail is easily accessible from Route 128. Parking is available on-site, though you should be aware that fees might apply during peak seasons. The park also provides convenient amenities such as picnic areas and restrooms for visitors. If you plan to bring your dog, they are welcome to join you on the trail, provided they remain on-leash.

This trail is located within Stage Fort Park in Gloucester, Massachusetts, a place known for its blend of natural beauty and historical significance. The route allows you to experience rugged coastline alongside lush pathways, making it a unique local attraction. In the summer months, the park's well-manicured gardens and wildflowers add an extra layer of scenic appeal to your hike.

Easy

2

hikers

5.99km

01:35

60m

50m

Embark on the Haskell's Pond Loop for an easy hiking experience through beautiful wooded surroundings, offering scenic views of Haskell Pond. This route covers 3.7 miles (6.0 km) with a gentle elevation gain of 205 feet (62 metres), making it a perfect choice for a quick outdoor escape. You can expect a diverse trail that begins with a wide, easy path before transitioning into narrower sections featuring some hills and numerous rock outcroppings. Along the way, you will also encounter several streams that flow into the reservoir, adding to the natural beauty of the landscape. The estimated duration for completing the loop is around 1 hour and 35 minutes.

Planning your visit to Haskell's Pond Loop is straightforward, as the trail is well-marked with distinctive yellow diamond-shaped markers, ensuring easy navigation throughout your hike. Parking for the trail is generally available directly at the trailhead, providing convenient access. If you are seeking a shorter or less strenuous walk, consider exploring just the first mile from the kiosk, which offers an easier option before the terrain becomes more varied. This flexibility allows you to tailor your experience to your available time and energy levels.

Haskell's Pond itself holds significance as a vital reservoir for the city of Gloucester, making your hike not just a recreational outing but also an encounter with an important local resource. The trail is situated within Mount Ann Park, providing a natural setting that supports diverse flora and fauna. As you traverse the path, you will notice the varied terrain, from wide, accessible sections to areas with more challenging rock outcroppings, reflecting the natural geology of the area. This loop offers a pleasant blend of natural scenery and practical utility within the park.

Easy

1.22km

00:20

20m

0m

Embark on an easy hike along the Red Maple Swamp Trail, a short 0.8-mile (1.2 km) route that takes about 19 minutes to complete. You will experience a gentle elevation gain of 77 feet (23 metres) as you explore the unique wetland ecosystem. The trail features elevated boardwalks that guide you through the swamp, offering close-up views of the red maples and surrounding woodlands. Look out for a distinctive tree branch that crosses the boardwalk, requiring you to duck as you pass underneath.

When planning your visit, be aware that parking is available but can be limited during peak times. It is advisable to bring insect repellent, especially in warmer months, as mosquitoes and biting flies can be present in the swampy environment. This trail is generally considered family-friendly and suitable for all skill levels, making it a great option for a quick outdoor escape.

The Red Maple Swamp Trail is located within Tompson Street Reservation and is particularly vibrant in the fall when the red maples display their stunning autumn colors. The elevated boardwalks are a key feature, allowing you to immerse yourself in the swamp without disturbing the delicate ecosystem. This route provides a unique opportunity to observe wetland flora and fauna in a protected natural setting.

Easy
Sign up for free to see 49 more hikes around Gloucester.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Close

Loading

Tips from the Community

Jamie S.
June 2, 2025, Cressy Beach

Cressy Beach is the larger of the two beaches located within Stage Fort Park. This scenic, rocky beach overlooks Gloucester Harbor and is a great place to relax and swim or explore and play games in the park. There are restrooms located in the park, just up the grassy hill from the beach, and there is also a privately owned restaurant nearby for you to enjoy.

0

0

Tyler Sanders
February 3, 2024, Haskell Pond

Haskell Pond is a large freshwater lake just west of Red Rocks and has miles of trails that encircle it, popular among hikers, runners, and bikers. Keep an eye out for a wide variety of wildlife as you go as well.

1

0

51m
January 26, 2024, Stage Fort Park

Stage Head was a fishing stage, named in 1624. The first fort was built here in 1635. Today it's a state park with two beaches, the reconstructed civil war fort and other leisure infrastructure.

0

0

Jamie S.
December 15, 2023, Dogtown Commons

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.

0

0

Jamie S.
October 11, 2023, Haskell Pond

Haskell Pond is a large freshwater lake just west of Red Rocks. There is a network of hiking, trail running, and mountain biking trails around the pond as well as an old public road that once gave access to this city reservoir. As you hike, be on the lookout for bird and other animals, as well as rock climbers working on boulder "problems" (shorter routes on boulders where you do not need ropes, only thick pads below) in the woods surrounding the pond. You can access the trails and old roads around Haskell Pond from the east through Red Rocks or from the north from Essex Ave and Forest Lane.

0

0

Jamie S.
October 9, 2023, Stage Fort Park

Overlooking one of the basefall fields in Stage Fort Park is a large bronze plauque on a huge grantite cliff that reads: "On this site in 1623, a company of fishermen and farmers from Dorchester, England, under the direction of Rev. John White, founded THE MASSACHUSETTS BAY COLONY. From that time the fisheries, the oldest industry in the commonwealth, have been uninterruptedly pursed from this port. Here in 1625, Gov. Roger Conant, by wise diplomacy, averted bloodshed between contending fractions, one led by Myles Standish of Plymouth, the other by Capt Hewes, a notable exemplification of arbitration in the beginnings of New England. Placed by citizens of Gloucester, 1907." This plaque speaks to the rich history of the area and believe it or not, you can sometimes see rock climbers ascending the rock faces next to the historic plaque!

0

0

Jamie S.
October 9, 2023, Stage Fort Park

Stage Fort Park is a park in Gloucester with a rich history. Gloucester's Visitor and Welcome Center and a reconstructed Civil War fort, Stage Fort, are both within park grounds. The park also has a playground, picnic benches, baseball fields, a dog park, and a bathhouse. There are two beaches in the park, Cressy and Half Moon Beach, stunning viewpoints, as well as a huge granite stone (with a plaque) thought to have been used by Native Americans, and cannons leftover from a Civil War-era fort. There is a privately owned seasonal restaurant, The Cupboard of Gloucester, where you can order fried clams and sandwiches.

1

0

Jamie S.
October 8, 2023, Viewpoint

From this viewpoint above Half Moon Beach in Stage Fort Park you get fantastic panoramic views over Gloucester Harbor, the Atlantic Ocean, and of downtown Gloucester. In addition to the fantastic views, you can also see some old cannons here that are left over from the military fort that once stood here.

0

0

Frequently Asked Questions

How many easy hiking trails are there in Gloucester?

Gloucester offers a wide selection of easy hiking trails. There are over 45 easy routes available, providing diverse options for outdoor exploration.

What kind of landscapes can I expect on easy hikes around Gloucester?

Easy hikes around Gloucester feature a varied landscape, from rugged coastlines and sandy beaches to dense, hilly forests and serene riverside paths. You can explore areas like Ravenswood Park with its woodland trails, or coastal paths offering stunning ocean vistas.

Are there easy circular walks in Gloucester?

Yes, many easy trails in Gloucester are circular, allowing you to start and end at the same point. A great option is the Babson Boulder and Dogtown Road Loop, which explores a historic forested area with unique rock formations.

Are the easy trails in Gloucester suitable for families with children?

Absolutely. Many easy trails in Gloucester are family-friendly, offering gentle terrain and interesting sights. The Stage Fort Trail, for example, leads through parkland and along the waterfront, which can be enjoyable for all ages.

Can I bring my dog on easy hikes in Gloucester?

Many easy hiking trails in Gloucester are dog-friendly, but it's always best to check local regulations for specific parks or reserves. Areas like Ravenswood Park are popular with dog walkers, offering wide carriage paths.

What do other hikers say about the easy trails in Gloucester?

The easy trails in Gloucester are highly rated by the komoot community, with an average score of 4.5 stars from over 10 reviews. Hikers often praise the varied terrain, from coastal views to quiet woodlands, and the well-maintained paths.

Where can I find easy hikes with coastal views or near water?

Gloucester boasts a beautiful coastline with several easy trails offering ocean views. The Magnolia Woods and Rafes Chasm Trail Loop provides both coastal vistas and woodland scenery. You can also explore areas like Rockport Harbor or Lobster Cove (Annisquam Harbor) for waterside walks.

Are there easy trails with interesting historical or natural landmarks?

Yes, Gloucester's easy trails often lead to fascinating landmarks. The Babson Boulder and Dogtown Road Loop takes you through Dogtown Commons, an area known for its glacier-formed rock formations and historical significance. You can also find highlights like Babson Farm Quarry Pond along some routes.

Are there easy trails accessible by public transport in Gloucester?

While specific public transport access varies by trail, many areas within Gloucester are served by local bus routes. It's advisable to check local bus schedules and routes to plan your journey to trailheads, especially for parks closer to the city center.

Are there easy hikes with parking available?

Most popular easy hiking areas in Gloucester, such as Halibut Point State Park, Ravenswood Park, and Stage Fort Park, offer dedicated parking facilities. It's generally easy to find parking near the starting points of many trails.

What is the best time of year for easy hikes in Gloucester?

Gloucester offers enjoyable easy hiking experiences year-round. Spring brings blooming wildflowers, summer provides pleasant coastal breezes, autumn showcases vibrant foliage, and winter can offer peaceful, crisp walks, especially in sheltered woodland areas like Ravenswood Park.

Are there any easy trails that lead to viewpoints?

Yes, several easy trails offer rewarding viewpoints. For example, the Ledge Hill Trail in Ravenswood Park provides views of Gloucester Harbor. Additionally, areas like Shore Road - Magnolia Point Gloucester offer expansive ocean views.

Are there easy trails with cafes or amenities nearby?

Many easy trails, particularly those closer to Gloucester's town centers or popular parks, have cafes, restrooms, or picnic areas nearby. For example, trails around Stage Fort Park are close to amenities, and Halibut Point State Park has a visitor center.

Most popular routes around Gloucester

Hiking around Gloucester

Most popular attractions around Gloucester

Places to see

Store rating

Get inspired with the komoot mobile app

With aΒ free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Hikes in other regions.

Georgetown-Rowley State ForestBoxfordIpswichEssexCrane Wildlife RefugeDogtown WoodsWillowdale State ForestMethuenCleaveland Farm State ForestRockportHaverhillHalibut Point State ParkNewburyportAmesburyBradley Palmer State ParkTopsfieldRiverfront State ParkLawrenceAndoverRowleySaugusMaudslay State ParkParker River National Wildlife RefugeBeverlyHarold Parker State ForestLynnSalemPeabodySwampscottDanversLynnfieldMarbleheadBaldpate Pond State ParkNahantSalisbury

Nearby adventure guides

Things to Do in Dogtown Woods

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

Β© komoot GmbH

Privacy Policy