Freeport – Hiking in Maine

Pettengill Farm (Freeport, ME)

January 9, 2025Undercover Hiker2 Comments

The Rodick Pettengill Farm in Freeport is a 140-acre property on the Harraseeket River owned and maintained by the Freeport Historical Society, and open to the public dawn to dusk, year-round. A self-guided tour and map, including trails, is available on the Freeport Historical Society website. In late October, we took a morning loop through the farm in the autumn foliage, using the Grant’s Point and Carter’s Creek Trails. Dogs are allowed (we were without Pig the dog for this hike, but saw several others with owners on the walk), a point we clarified with the Freeport Historical Society, as this policy has changed over the last several years.

Saltbox house, Pettengill Farm, Freeport, ME

Parking is available on Pettengill Road at the end of the farm’s driveway (as is a house-shaped box for donations) – just don’t park in front of the gate. Many historical placards dot the property, with vignettes from the farm’s up-and-down history, archeological findings, interactions with Native populations, and signs pointing out the sites of former buildings. The long driveway leads to the open fields around the farmhouse, built around the year 1800. We peeked in the windows (tours are available for groups of two or more with advance notice), then we walked downhill to the Harraseeket River, the site of a former shipping wharf for a brickyards.

Harraseeket River, Pettengill Farm, Freeport, ME

The sunlit October morning had a chill to it, but was invigorating, particularly since many hike reviews in warmer months listed mosquitoes and other biting insects as omnipresent. Across the field to the northeast of the house, we picked up the Grant’s Point Trail, mostly downhill through the mixed evergreen woods with a couple twists and the strong smell of pine, taking it all the way to its namesake promontory, with an excellent view of the river and beyond.

There were some muddy areas, but none that were problematic or couldn’t be traversed. We took the Carter’s Creek Trail, winding in a forest full of birdsong, back up to the fields, skirting the edge until reaching the long driveway again. We bypassed the Ridge Trail and Marsh Trails, leaving them for another time.

Grant’s Point, Pettengill Farm, Freeport, ME

All told, the lollipop-type loop hike was about three miles in an easy hour and ten minutes, with time to read about history, stop in the sun, and birdwatch. While we did see other walkers and hikers, it was very quiet in the wooded portion of the trail. For those interested in more Freeport-area historical sites, the Freeport Historical Society has a Freeport Heritage Trail, with a map of sites and accompanying audio files.

Wolfe’s Neck Woods State Park

July 2, 2023July 14, 2025Undercover HikerLeave a comment

(Note: as of July 2025, ongoing construction affects accessibility and capacity at Wolfe’s Neck. You can receive park Park & Trail Conditions by sending a Text WOLF to 888-514-7527.)

For good reason, Wolfe’s Neck Woods State Park is a popular year-round destination for both Mainers and visitors. Close to the shopping mecca of Freeport and L.L. Bean’s adventure excursion launchpads, the state park can sometimes become crowded with people seeking an accessible outdoors spot (it’s listed as #1 of 21 things to do in Freeport by TripAdvisor). There are, however, quiet parts of this over 200-acre coastal sanctuary. A detailed map and description can be found in the worthwhile Falcon Guides’ Hiking Maine, or free, along with a calendar of activities, on the Wolfe’s Neck Woods State Park website. Entry to the park, which is open for day use, is $4 for Maine residents (free for veterans). Dogs must be leashed, and owners must pick up after their pets. No bicycles are allowed on the Wolfe’s Neck hiking trails. Restrooms are located near the parking area, and picnic areas are interspersed through the park nearby.

Googins Island from shore by Casco Bay Trail, Wolfe’s Neck Woods State Park

On a busy weekend at the beginning of July, we used the White Pines Trail, North Loop Trail, Casco Bay Trail, and Harraseeket Trail to make an easy 3 mile perimeter loop, taking about an hour and a half to enjoy, and as usual, navigating using the AllTrails app. As soon as we left the parking area via the White Pines Trail, we began to hear a variety of birds, including red-eyed vireo, dark-eyed junco, black-throated green warbler, and inland, a broad-winged hawk. On the shoreline, we heard and saw osprey, including one returning to the treeline with a large fish. Further along, on the Harraseeket Trail, we heard the distinctive song of a hermit thrush, chipping sparrows, blackburnian warbler, and a blue-headed vireo.

Casco Bay view, Wolfe’s Neck Woods State Park

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Winslow Memorial Park Loop

May 1, 2022August 11, 2022Undercover Hiker1 Comment

Winslow Memorial Park and Campground, owned by the town of Freeport, Maine, is a 100-campsite campground, beach, and park on a narrow peninsula between the Harraseeket River and Casco Bay. During 2022, Winslow Park will be open for camping from May 26th through October 1st. A map of the property, including trails, can be found here. According to the Town’s website, the 90-acre park was a 1953 gift from Adelaide Winslow Harb in memory of her mother, Delia B. Powers Winslow with the understanding that the land and its buildings, “… shall be used as a public park and for public recreational purposes…” A day-use fee is charged during the summer months (Freeport Residents: $2.00 per person; Non-Residents: $3.00 per person). Day use hours are from 8 a.m. to 30 minutes after sunset for use of all facilities, including trails.

Reflection bench, Winslow Park, Freeport, ME

The trails at Winslow Park are named in a simple fashion, and we made a loop of the Scenic Trail and Self-Guided Nature Trail, using Winslow Park Way to connect these short loops, for a 2.5 mile hike lasting about an hour. The footing was a bit mucky on the late April day we visited, but it was a small price to pay to avoid crowds and fees and see the stunning coastal views. We started with the Scenic Trail, accessed from the parking lot to the immediate left of the entrance gate. A wide, flat trail encircles the small wooded peninsula jutting out into the Harraseeket River. We continued on Winslow Park Way, then veered left past a picnic area towards a sign marked “Trails” to rejoin the Scenic Trail, which then became the Self-Guided Nature Trail.

View of Harraseeket River and Staples Cove from Winslow Park, Freeport, ME

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Florida Lake Loop

April 18, 2022May 10, 2023Undercover Hiker3 Comments

Tree swallows feeding by nesting boxes, Florida Lake, Freeport, Maine

Florida Lake Loop is part of a 167-acre property owned by the Town of Freeport since 2002, with trail maps available from the Freeport Conservation Trust. This 2.9 mile loop, using the orange Lake Loop and blue-blazed North Loop trails, skirts the edge of shallow Florida Lake, passing through wetlands and forest. The trails are accessible from a well-marked turnoff (blue sign for Florida Lake parking) off Route 125/Wardtown Road in north Freeport, leading to a small (six cars or so) parking lot. A map kiosk is located a short walk down the gravel trail towards Florida Lake (this map is faded, so the orange trail appears as yellow). This lake gets its name from the resemblance of its meandering finger-like shape to the familiar southern U.S. state.

Small pond off spur trail, Lake Loop Trail, Florida Lake, Freeport, ME

On the Easter Sunday we visited, mud season was very much in effect, necessitating waterproof boots and a certain agility in negotiating logs over standing water. The turtles sunning themselves on the small outlet of the lake gazed at us with exasperation, then slowly slide into the cold water, no doubt gurgling mild turtle swears as they dove. Nesting boxes line the lake itself, and tree swallows wheeled past our heads in blurs of blue-green and white, feeding and diving inside the small shelters.

Orange-blazed Lake Loop Trail, Florida Lake, Freeport, ME

Heading counter-clockwise around the orange trail, a small spur led to a secluded pond, and we doubled back through the muck to continue around Florida Lake. Princess pine lined the trail, and soon we encountered exotic-looking bright green and reddish skunk cabbage plants emerging in the wetlands to each side of the log bridges leading around the south side of the loop.

Skunk cabbage ascending, Lake Loop Trail, Florida Lake, Freeport, ME

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