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Routes
Running trails & routes
United States
Maine
Lincoln County

Gregory Trail loop & Oak Point Farm loop

Routes
Running trails & routes
United States
Maine
Lincoln County

Gregory Trail loop & Oak Point Farm loop

Moderate

4.7

(6786)

7,229

runners

Gregory Trail loop & Oak Point Farm loop

00:53

7.96km

80m

Running

Jog this moderate 4.9-mile loop through varied terrain, from wooded paths with river views to open fields and coastal scenery.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

Get Directions

1

17 m

View of Back River from Gregory Trail

Highlight (Segment) • Viewpoint

If you follow the trail with white blazes at Boothbay Regional Land Trust, you'll keep on the Gregory Trail the entire time. This path makes a short loop that spends …

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2

4.23 km

Dock at Oak Point Farm

Highlight • Rest Area

There is a cool view of the harbor and bay from this boat dock in the preserve.

Oak Point Farm is a nature preserve nestled up against Obies Cove. There …

Tip by

B

7.96 km

End point

Parking

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Way Types & Surfaces

Way Types

5.73 km

2.22 km

Surfaces

5.43 km

1.12 km

1.10 km

305 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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Today

Wednesday 13 May

13°C

3°C

79 %

Additional weather tips

Max wind speed: 14.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the terrain like on this jogging route?

The combined route offers a varied experience. You'll encounter dirt and forest floor paths within the Gregory Trail loop, winding through dense woods. At Oak Point Farm, the trails feature mowed fields, forest paths, crushed stone sections, and grassy areas, with some boardwalks. The description for the combined route also notes "mostly paved surfaces," suggesting that connecting sections between the two preserves are on local roads.

Are dogs allowed on the Gregory Trail loop & Oak Point Farm loop?

Yes, dogs are generally welcome on the trails within both the Gregory Trail loop and Oak Point Farm loop. However, it's crucial to keep them on a leash at all times and to practice Leave No Trace principles, including picking up after your pet. Always check for any updated signage or specific regulations from the Boothbay Region Land Trust before your visit.

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

The trails are enjoyable year-round. Late spring through fall offers pleasant weather for jogging, with opportunities to see wildflowers and monarch butterflies in late summer and early fall. In winter, Oak Point Farm also offers activities like cross-country skiing and snowshoeing, so the trails are accessible, but conditions may vary and require appropriate gear.

Do I need a permit or is there an entrance fee for these trails?

No, there are typically no permits or entrance fees required to access the Gregory Trail loop or the Oak Point Farm loop, as both are managed by the Boothbay Region Land Trust and are open to the public for recreational use.

Where can I park to access the Gregory Trail loop & Oak Point Farm loop?

Specific parking information for the combined route isn't detailed, but both the Gregory Trail and Oak Point Farm have their own access points. It's recommended to check the Boothbay Region Land Trust's website or local maps for designated parking areas near the trailheads in West Boothbay Harbor, Maine.

What kind of wildlife can I expect to see along the way?

You can observe a variety of wildlife. On the Gregory Trail, look for deer, small mammals, and various bird species, especially around the small pond which hosts bullfrogs and dragonflies. At Oak Point Farm, the freshwater pond is home to ducks, beavers, frogs, and turtles, while the coastline attracts a wide variety of sea and land bird species. Monarch butterflies are also common in late summer and early fall.

What are the main points of interest or viewpoints on this route?

Along the route, you'll find several scenic spots. The Gregory Trail offers serene views of the Back River. At Oak Point Farm, you'll enjoy captivating views of Hodgdon Cove and its wildlife, as well as a freshwater pond. Specific highlights include the View of Back River from Gregory Trail and the Dock at Oak Point Farm.

Does this jogging route intersect with other trails?

Yes, the route utilizes and intersects with several named trails, particularly within the Oak Point Farm section. You will encounter sections of the White Blazed Trail, Story Trail, UA Loop, Becky's Way, Huckleberry Cove Trail, and Cedar Ledge Trail.

Is this route suitable for beginners or families?

While the individual loops (Gregory Trail and Oak Point Farm) are generally considered easy and suitable for all skill levels, the combined route is rated as moderate due to its distance (nearly 8 km) and elevation gain (80m). It requires good fitness for a continuous jog. However, the universally accessible sections at Oak Point Farm make parts of it very family-friendly and inclusive.

What is the Boothbay Region Land Trust's role in managing these trails?

The Boothbay Region Land Trust (BRLT) is responsible for managing both the Gregory Trail and Oak Point Farm properties. Oak Point Farm serves as the BRLT's headquarters. They maintain the trails, protect the natural habitats, and ensure public access for recreation, often offering year-round activities and educational opportunities.

Are there any specific considerations for combining the two loops into one jogging route?

When combining the Gregory Trail loop and Oak Point Farm loop, be aware that while the individual trails are natural and easy, the full 7.96 km route likely connects these preserves via local roads. This accounts for the "mostly paved surfaces" mentioned and contributes to its "moderate" difficulty rating. Be prepared for sections on pavement between the natural trail segments.

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