The best parks & outdoor spots in Winslow

6 places we’ve checked and would send a neighbor to. Open any one to read what we wrote about it.

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Quarry Road Trails (opens in a new tab)

300 Quarry Rd · Waterville

Quarry Road Trails keeps the outdoor stoke alive in Waterville with 13.3 km of groomed Nordic loops, a rope tow ski hill, 8 km of…

3 km of groomed Nordic loops, a rope tow ski hill, 8 km of singletrack for biking and hiking, disc golf, paddling, and a busy calendar of races and programs for all ages. Reliable snowmaking means fewer winter excuses.

From the Skowhegan newsletter, October 9, 2026

Inland Woods Walking Trails (opens in a new tab)

1 Jewells Way · Waterville

When you just need a quick reset without leaving town, Inland Woods Walking Trails delivers a peaceful, get-your-steps-in fix right in…

When you just need a quick reset without leaving town, Inland Woods Walking Trails delivers a peaceful, get-your-steps-in fix right in Waterville, maintained by the all-volunteer Kennebec Messalonskee Trails, a local 501(c)(3) that makes everyday walks feel a little more like an adventure.

From the Winslow newsletter, October 23, 2026

Messalonskee Stream Trail (opens in a new tab)

1115-1119 Kennedy Memorial Dr · Oakland

When your brain needs fresh air more than another email, Messalonskee Stream Trail is a well-loved path in the Kennebec Messalonskee Trails…

When your brain needs fresh air more than another email, Messalonskee Stream Trail is a well-loved path in the Kennebec Messalonskee Trails network, maintained by local volunteers. Hit the KMT map, grab the route info you need, and enjoy a mindful walk on lands of the Wabanaki Confederacy.

From the Waterville newsletter, October 23, 2026

Kennebec River Rail Trail (opens in a new tab)

Kennebec River Rail Trail · Augusta

Six and a half miles of path hugging the Kennebec, the Kennebec River Rail Trail links Augusta’s Waterfront Park through Hallowell and…

Six and a half miles of path hugging the Kennebec, the Kennebec River Rail Trail links Augusta’s Waterfront Park through Hallowell and Farmingdale to Gardiner, good for walking, running, cycling, skateboarding, rollerblading, or dog walking.

From the Sidney newsletter, October 7, 2026

Viles Arboretum (opens in a new tab)

153 Hospital St · Augusta

Viles Arboretum is 224 acres of trails, cultivated gardens, orchards, groves, and research plots where you can hike, bike, or snowshoe…

Viles Arboretum is 224 acres of trails, cultivated gardens, orchards, groves, and research plots where you can hike, bike, or snowshoe year-round, with rentals available. It’s a legit free botanical garden right here in Augusta, perfect for quick lunch walks, kid energy burn-offs, or weekend rambles.

From the Augusta newsletter, October 13, 2026

Augusta Nature Ed. Center Entry 13 (opens in a new tab)

Haskell St · Augusta

When you need a quick reset close to home, Augusta Nature Ed. Center Entry 13 opens onto quiet, well-kept trails where the seasons actually…

When you need a quick reset close to home, Augusta Nature Ed. Center Entry 13 opens onto quiet, well-kept trails where the seasons actually show off, and the trail map keeps you wandering on purpose. Check out their field trips and programs if you’ve got kids or curiosity to spare.

From the Augusta newsletter, October 20, 2026