Best Hiking Trails in Gloucester, MA: Top Scenic Outdoor Adventures



1. Ravenswood Park – Classic Forest Loop in Gloucester

Ravenswood Park is a local favorite, offering ~10 miles of trails with flexible loop options (~2–4 mi) for casual or more serious hikers. Trails pass serene ponds, swamps, and granite outcroppings, with clear trail markers guiding your way. Accessible parking areas make it a convenient starting point for all visitors.

Highlights:

• Forest, swamp, and pond habitats
• Flexible loop hikes for all skill levels
• Clear trail markers and an accessible parking area

Hikers enjoy a mix of wooded trails, open clearings, and natural scenery. The loops make it suitable for both short walks and longer outdoor adventures.

2. Dogtown Trailhead & Dogtown Loop – Historic Boulder Trails

The Dogtown Loop is a historic loop hike passing through Dogtown Common. Hikers can start from Bray Street or Tompson Street, both with convenient parking areas. The trail features massive granite outcroppings, inspirational rock inscriptions, and peaceful woodland paths.

Highlights:

• Historic stone walls and boulders
• Flexible loop trail options
• Scenic forest paths

This trail is perfect for hiking, photography, and exploring Gloucester’s outdoor history, offering both challenge and tranquility.

3. Mount Ann Park – Rolling Forested Loop

Mount Ann Park features a moderate trail loop ideal for hikers seeking a peaceful woodland walk. Trails are marked with trail markers and wind through rolling hills, mixed forests, and quiet paths near the pond.

Highlights:

• Moderate loop hike with forest trails
• Gentle hills and scenic overlooks
• Well-marked trails

Hikers enjoy a calm environment with opportunities to spot local wildlife while exploring Gloucester’s inland trails.

4. Rafes Chasm Park – Quick Coastal Adventure

This 0.9‑mile loop trail combines forest paths with Cape Ann coastal scenery, ending at impressive ocean cliffs and chasm formations. Ideal for a short, rewarding hike with striking views.

Highlights:

• Short loop hike (~0.9 mi)
• Dramatic cliffs and chasm formations
• Coastal and forest scenery

The trail provides a mix of quick adventure and scenic views, perfect for hikers with limited time but who want memorable landscapes.

5. Goose Cove Reservoir – Easy Lakeside Loop

The Goose Cove Reservoir trail is an easy hiking loop, great for beginners or family outings. The path circles the reservoir, passes through peaceful woodland areas, and offers wildlife-spotting opportunities. Nearby parking areas make access simple.

Highlights:

• Calm reservoir views
• Easy, beginner-friendly loop hike
• Forested paths with wildlife spotting

Hikers can enjoy a serene, accessible trail with gentle terrain suitable for all ages.

6. Crane Beach Loop – Coastal Dunes & Pine Forest

Located in Ipswich, the Crane Beach Loop is a moderate loop hike featuring maritime pine forest, soft dunes, and stretches of pristine beach. Hikers follow clear trail markers along the Green and Red Trails, with optional spur paths for additional exploration.

Highlights:

• Coastal dunes and forest trails
• Beachside views along a loop trail
• Moderate hiking with optional spur loops



This trail provides a refreshing coastal experience, blending forest, sand, and ocean scenery for hikers seeking both variety and natural beauty.

7. Eagle Rock Trail – Scenic Coastal & Forest Hike

Eagle Rock Trail is a moderate loop hike featuring coastal cliffs, pine forests, and panoramic views of Gloucester Harbor. The trail is well-marked with trail markers and accessible from nearby parking areas, making it ideal for a rewarding half-day hike.

Highlights:

• Coastal cliffs and panoramic harbor views
• Forested paths with rocky outcroppings
• Moderate loop suitable for most hikers

Hikers enjoy a mix of ocean vistas, shaded forest paths, and granite outcroppings, offering both scenic beauty and a bit of adventure. The loop allows for flexibility in distance, so you can extend or shorten your hike as needed.

Final Thoughts

Gloucester offers hiking trails for all levels—from the forested Ravenswood Park and historic Dogtown Loop to coastal views at Rafes Chasm and Crane Beach Loop, plus serene Goose Cove Reservoir and Eagle Rock Trail. With clear markers, easy parking, and well-connected paths, exploring Gloucester’s landscapes is both simple and rewarding.

After a day outdoors, you can dive into Gloucester’s top things to do, enjoy the best local restaurants, or unwind at nearby Luxury Vacation Rentals for a relaxing stay. Blending scenic hikes, outdoor activities, and great food, Gloucester delivers a complete and memorable Cape Ann experience for both visitors and locals.

FAQs About Hiking in Gloucester, MA

• What are the best hiking trails in Gloucester?
  Top trails include Ravenswood Park, Dogtown Loop, Mount Ann Park, Rafes Chasm, Goose Cove Reservoir, Crane Beach Loop, and Eagle Rock Trail.
• Are these trails good for beginners?
  Yes! Trails like Ravenswood Park, Goose Cove Reservoir, and Mount Ann Park offer gentle loops suitable for beginners and casual hikers.
• Where can I find trail maps?
  Most hikers use AllTrails for up-to-date maps, trail distances, and conditions. Printed maps are also available at local visitor centers.
• Are dogs allowed on the trails?
  Many trails are dog-friendly, including Ravenswood Park and Dogtown Loop. Leash rules vary, so check trail signs before starting.
• What’s the best time to hike in Gloucester?
  Late spring through fall is ideal. Summer offers long daylight hours, while fall provides stunning foliage and coastal views.
• Is parking available at the trailheads?
  Yes, all main trails have parking areas, but weekends can be busy—arrive early for the best spots.
• Are Luxury Vacation Rentals near the trails?
  Yes! Gloucester has several Luxury Vacation Rentals providing easy access to hiking trails, beaches, and local attractions for a comfortable stay.