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Routes
Running trails & routes
United States
Massachusetts
Essex County
Gloucester

Leonard Street to Brierwood Street loop

Moderate

4.7

(7313)

11,732

runners

Leonard Street to Brierwood Street loop

00:37

5.52km

80m

Running

Jog the moderate 3.4-mile Leonard Street to Brierwood Street loop in Annisquam, featuring scenic woods and the Annisquam Footbridge.

Last updated: February 26, 2026

Waypoints

A

Start point

Bus stop

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1

1.89 km

Annisquam Footbridge

Highlight • Bridge

Bicycles are allowed on the bridge. Nice views of Lobster Cove.

Tip by

B

5.52 km

End point

Bus stop

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Way Types & Surfaces

Way Types

3.72 km

1.07 km

529 m

209 m

Surfaces

3.54 km

1.07 km

514 m

404 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

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Tuesday 19 May

31°C

12°C

-- %

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to jog this loop?

Most joggers complete the Leonard Street to Brierwood Street loop in about 35-40 minutes. The route is approximately 5.5 kilometers (3.4 miles) long.

Is this jogging loop suitable for beginners?

Yes, while rated as 'moderate' due to some elevation changes, the loop is generally considered suitable for all skill levels. The terrain is mostly paved, offering a stable and accessible path for those new to jogging or looking for a comfortable run.

Where can I park to access the trail?

Parking information for this specific loop isn't detailed in our current data, but Annisquam Village generally has limited street parking. It's advisable to look for public parking areas within Annisquam Village, keeping in mind local regulations.

What kind of terrain can I expect on the loop?

You'll find mostly paved surfaces, making for a smooth jogging experience. The route winds through wooded hillsides and mature forests, with some elevation changes that contribute to its moderate difficulty rating for runners. You might also encounter natural features like granite outcroppings and old stone walls.

What are the scenic highlights or viewpoints along the way?

The loop offers a blend of natural beauty and historic charm. You can expect views of winding trails, wooded areas, and potentially glimpses of Langsford Pond, known for beavers and waterfowl, and the broader Annisquam River, a saltwater tidal estuary. A notable feature is the Annisquam Footbridge.

What is the best time of year to jog this route?

The Annisquam area is beautiful year-round. Spring and fall offer pleasant temperatures and vibrant foliage, while summer can be lovely, especially in the mornings or evenings. Winter jogging is possible, but be mindful of snow and ice conditions.

Are there any specific landmarks or features to look out for?

Beyond the scenic views, keep an eye out for historic elements like old stone walls and exposed granite outcroppings, sometimes locally referred to as 'Squam rock' with 'practice boulders'. The route also passes by the Annisquam Footbridge.

Is the Leonard Street to Brierwood Street loop dog-friendly?

Our data doesn't specify dog rules for this exact loop. However, many trails in the Annisquam Woods area are dog-friendly, usually requiring dogs to be on a leash. It's always best to check local signage or the Essex County Greenbelt website for the most current regulations.

Do I need any permits or pay an entrance fee to jog here?

Based on available information, there are no specific permits or entrance fees required to jog the Leonard Street to Brierwood Street loop. It appears to be freely accessible.

What kind of wildlife might I see on the trail?

The Annisquam area is rich in natural beauty. Along the route, especially near Langsford Pond, you might spot waterfowl and even beavers. The wooded sections could offer glimpses of common New England wildlife.

Does this route connect with other trails?

Yes, the route also passes through sections of the Cart Track Drive, the Annisquam Footbridge, Lobster Cove, ManBearPig, and Pit Link trails, offering opportunities to explore further if you wish.

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