Crosby Landing Trail

Where else can you walk in Brewster?

• Easy · 0.5 mi

  Stony Brook Herring Run & Grist Mill Walk

  Mixed · Town of Brewster

  A short, historically rich walk along Stony Brook past the restored 1873 Grist Mill, where herring (alewives) migrate upstream from Cape Cod Bay to freshwater ponds each spring. Footpaths line both sides of the brook, with a footbridge offering viewing platforms over the fish ladder weirs. Best visited mid-March through early May during the herring run, but scenic year-round.

  CCC Visited · Verified 2026-06-25

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• Easy

  Cape Cod Rail Trail (Brewster)

  Paved · Massachusetts DCR (Department of Conservation and Recreation)

  The Cape Cod Rail Trail is a paved, multi-use path running about 25 miles from Dennis to Wellfleet along a former railroad bed. Its Brewster stretch passes forests, cranberry bogs and ponds, and in East Brewster it connects to the 8 miles of paved trails inside Nickerson State Park. Flat and fully paved, it is ideal for family biking, walking, jogging and wheelchair use.

  CCC Visited · Verified 2026-10-06

  Where to park on the Cape Cod Rail Trail

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• Easy · 0.4 mi

  Drummer Boy Park Loop Trail

  Paved · Town of Brewster Recreation

  A universally accessible 0.4-mile paved loop through a 17-acre historic park anchored by a restored 1795 smock windmill. The path offers open views across Quivett Creek salt marshes and Cape Cod Bay in the distance. Free admission makes this a relaxed stop for all ages. Home to summer craft fairs and Sunday evening band concerts.

  Listed & Verified · Verified 2026-06-25

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• Moderate · 2.5 mi

  Punkhorn Parklands – Eagle Point to Seymour Pond Trail

  Natural trail · Town of Brewster Conservation

  The premier long walk in the Punkhorn Parklands — over 800 acres of Town-owned conservation land in West Brewster. This route winds through oak and pitch pine forest past Upper Mill Pond and Seymour Pond, with sweeping views from Eagle Point. Multiple intersecting trails allow shorter loops from the Run Hill Road parking area. A rare quiet inland wilderness on the Outer Cape.

  Listed & Verified · Verified 2026-06-25

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• Easy · 1.5 mi

  Namskaket Creek Beach Walk

  Sand · Town of Orleans / Orleans Conservation Trust

  A 1.5-mile round-trip beach walk from Skaket Beach across soft tidal sand to Namskaket Creek, a 200-acre saltmarsh straddling Orleans and Brewster. One of the most ecologically significant tidal corridors on the inner Cape, rich with shorebirds, herons, and migratory waterfowl. Part of the emerging Cape Cod Sea Path multi-town coastal route.

  Listed & Verified · Verified 2026-06-25

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• Moderate

  Nickerson State Park Trails

  Mixed · Massachusetts DCR (Department of Conservation and Recreation)

  Nickerson State Park covers roughly 1,900 acres of pine and oak forest dotted with eight freshwater kettle ponds. About 8 miles of paved bike paths wind through the woods past Cliff Pond, Flax Pond and Little Cliff Pond, connecting directly to the Cape Cod Rail Trail. The park also has natural hiking trails and singletrack, plus swimming, fishing and over 400 campsites. A premier spot for biking, hiking and birding in Brewster.

  Listed & Verified · Verified 2026-06-19

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