Every place below is listed and verified by Cape Cod Certified.
Visiting Cape Cod
Plan where to eat before, during, and after your Cape Cod Rail Trail ride. Expert picks in Dennis, Brewster, Orleans, Eastham, and Wellfleet — by mileage.
Cape Cod Celebrations
A transparent, line-by-line look at real Cape Cod wedding costs in 2026 — venue, catering, clambake, florals & more, with budgets for 50, 100 & 150 guests.
Living on Cape Cod
Cape Cod septic guide for 2026: Title 5 rules, I/A nitrogen-reducing systems, real install costs, watershed permits, tax credits, and what to do before you sell.
Beach DayA private tour from the Meetinghouse Pond town dock through Orleans' waterways to the barrier beach, Chatham fishing fleet and seal colonies. Personal and flexible, ideal for families.
Beach DayThree trailside shops put the Outer Cape's best riding at your doorstep, with free locks and trail maps on every rental. From the Rail Trail to the National Seashore, grab a bike and go.
Freshwater Pond
A quiet freshwater kettle pond with warm, clear, calm water, a narrow beach strip, and a low-key feel. A good alternative for swimming and kayaking when ocean conditions are rough. Dogs prohibited June 15 through Labor Day.
Easy · Paved
The Orleans stretch of the 25.5-mile paved Cape Cod Rail Trail, a former railroad bed managed by Massachusetts DCR running from South Yarmouth to South Wellfleet. The trail crosses Main Street in downtown Orleans near mile 13 and passes the Orleans rotary, with a parking lot off Old Colony Way putting riders steps from shops and dining. Flat, paved, and fully wheelchair- and stroller-accessible. Dogs welcome on leash.
Easy · 0.5 mi · Natural trail
A short, peaceful walk through 10 acres of conservation land overlooking the entrance to Arey's Pond, a tidal cove connecting to Pleasant Bay. The John Kenrick Woods trail network to the north also terminates at a viewpoint above Arey's Pond. No facilities; stay on marked paths to protect sensitive shoreline. Best in early morning for birding over the pond.
Easy · 1.5 mi · Natural trail
A 1.5-mile loop system through pitch pine and oak woodland connecting Ice House Pond and Reuben's Pond. Bench overlooks each pond; plant ID tags throughout. A children's Storybook Trail loop (0.75 miles) takes families through picture-book stations at nature stations. Ice House Pond is among the healthiest in Orleans and popular with birders year-round for migrating waterfowl.
Easy · 1 mi · Natural trail
A 46-acre white pine-oak forest in South Orleans with a roughly 1-mile trail through a white pine grove. Notable for more than 75 American chestnuts — one of the few sites in Massachusetts where the species is reproducing. Part of a 600-acre greenbelt connecting to the Areys Pond watershed and Pleasant Bay, and rich in local history (site of the original South Orleans General Store). Dogs welcome on leash.
Moderate · 1 mi · Natural trail
A 31-acre OCT property in South Orleans with about a mile of trail in three short loops around a clean kettle pond. Pine and oak woodland with a locally rare Atlantic white cedar swamp, plant ID tags along the trails, and elevated pond views. Wildlife includes otters, woodpeckers, hooded mergansers, and great horned owls. Some steep sections. Dogs welcome on leash.
Freshwater Pond
A freshwater pond and town swimming beach offering calm, warm water and a small sandy beach. Seasonal lifeguard, picnic areas, and kayak/canoe access. A great backup when the saltwater beaches are crowded or rough. Dogs prohibited June 15 through Labor Day.