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Walking & hiking is an exercise in natural beauty in Greater Portland & Casco Bay

Portland Hillside
Fore Street, Old Port, and Congress Street Walk

Portland is so dense with elegant 19th-century urban architecture and waterfront views that any walk through the city is a scenic stroll. A couple of the standout areas are Fore Street along the waterfront, famous for its progressive food culture; the Old Port waterfront; and Congress Street, including the city's Museum of Art, City Hall, and other monumental buildings. These routes all pass waterfront and urban parks, with neat public sculpture and busy social scenes. See the attached map for points of interest.
wolfe neck woods state park
Wolfe's Neck Woods State Park

426 Wolfe's Neck Road Freeport, ME Phone: 207-865-4465

Good for picnicking, hiking and walking; an entry fee is charged.

Walk or hike along Casco Bay Trail. Follow scenic paths to views of nearby Eagle, Counsin, and other islands. The longer Harraseeket Trail offers one-and-a-half miles of bay views and is more difficult in comparison to the half-mile North Loop Trail, which is a less challenging walk with views of a nearby farm.
See trail map of Wolfe's Neck Woods State Park.
Fort Williams Park and Portland Head Lighthouse
Fort Williams Park and Portland Head Lighthouse

Off Shore Road Cape Elizabeth, ME Phone: 207-433-5910

Seaside park includes beloved lighthouse; good for walks, picnics, ocean views

The park on the ocean just south of Portsmouth contains the famous Portland Head Lighthouse and Museum, along with many pleasant paths for walking and bicycling. See full description of Fort Williams State Park.
Sebago to the Sea Trail (Pedestrian)

The 4.8 miles section from South Windham to Westbrook is now open for pedestrian use. The first 1.5 milesfrom South Windham is a flat, easy walking path on an undeveloped rail bed. The remaining 3.5 miles, to Bridge Street in Westbrook, is on railroad tracks. Members of the Sebago to the Sea Trail Coalition have been working to a continuous trail from Sebago Lake to Casco Bay. (Google map link shown here is approximate.) See map.
Bayside Trail

Trailheads at Elm Street and Casco Bay end of Marginal Way Portland, ME Phone:

This 1-mile trail is a flat, paved surface through the Bayside and East Bayside neighborhoods. It extends at the south end from Elm Street between Somerset Street and Marginal Way and parallels Marginal Way, linking with the East Promenade and the Back Cove Trails near the highway overpass where Route 1 crosses Back Cove. There are several benches and three water fountains. Trail is good for walkers, runners, and bicyclists.
Portland Trails Urban Land Trust

305 Commercial Street Portland, ME Phone: 207-775-2411

This organization maintains a 50-mile network of trails in Greater Portland with 31 trails. Highlights:
Eastern Promenade Trail is on a former rail corridor and it has harbor and ocean views. Benches and picnic tables are along the trail and at East End Beach. Fore River Sanctuary enbraces the Jewell Falls waterfall and the location of the old Cumberland and Oxford Canal. Good for bird watching. Back Cove Trail offers great views of the Portland skyline. Ideal for walking, running, biking (road/mountain) and dog walking. Presumpscot River Preserve follows a deep ravine into the Preserve and it is steep in places. Boardwalks and bridges pass over wet areas and permit mountain bike access.
Gilsland Farm Center of the Maine Audubon Society

20 Gilsland Farm Road Falmouth, ME, 04105 Phone: 207-781-2330

Nordic skiing and snowshoeing allowed on year-round walking trails; snowshoes, only, for rent.

This headquarters for Maine Audubon is just a few milesfrom Portland, located along the Presumpscot River estuary. It has an environmental center and a 65-acre sanctuary with two miles of trails winding through woods, meadows, and salt marsh. Trails are open for cross-country skiing and snowshoeing. Snowshoes available for rent. Trails open daily, dawn to dusk. Nature center open daily, 9 a.m.-5 p.m.; Sunday, noon-4 p.m.