Gregory Trail loop & Oak Point Farm loop
Gregory Trail loop & Oak Point Farm loop
4.7
(6786)
7,229
runners
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
Start point
Parking
Get Directions
17 m
Highlight (Segment) • Viewpoint
Tip by
4.23 km
Highlight • Rest Area
Tip by
7.96 km
End point
Parking
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
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.