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Highland Loop Map and Description

Detailed Route Description — 19.3 mile loop
Mill Creek Park to Black Point Road (5.8 mi.)
Leave Hannaford Supermarket parking lot heading west on Hinckley Drive. Turn left onto Ocean St., then continue straight through the light at Broadway on Ocean St/Rt 77 for .3 miles and turn right onto Highland Avenue.

Climb a steady hill, passing Hinckley Park on your left, then reaching flatter terrain near where Anthoine Street enters from the right. Pass South Portland High School on the right (a parking lot just before the school, also on the right, offers views of Mount Washington on the horizon.) Stay on Highland Avenue, passing through a thickly settled area, then a long straightaway that begins transitioning into farmland.

At 4.0 miles, Highland Avenue crosses over Pleasant Hill Road. You’ll pass a farm stand and greenhouse on the left and a golf course to your right. At 4.4 miles, you’ll reach an intersection. Bear left to stay on  Highland Avenue and follow it to its terminus at Black Point Road/Rt 207.  

Black Point Road to Shore Road (8.7 mi.)
Trip distance to this point: 14.5 miles.
A 1.8 mile ride on Black Point Rd/Rt 207 treats you to some beautiful views, including Scarborough Marsh. Turn left onto Rt 77/Spurwink Road, passing in succession Higgins Beach (accessible via a side trip on Ocean Avenue) and the entrance to Crescent Beach State Park.

After Passing a farm on the right and a large inn (also on the right), Rt 77 takes a sweeping left turn, passes another farm, then continues toward the junction with Shore Road (just past the shopping plaza on your left).

Shore Road to Mill Creek Park (4.9 mi.)

Trip distance to this point:19.3 miles.
Turn right onto Shore Road. There are narrow shoulders along this stretch. Please exercise extra caution when riding, particularly when encountering the hilly section just after you see the entrance to the Robinson Woods, an 82-acre preserve with 3 miles of trails and 300 year old trees owned by the Cape Elizabeth Land Trust.

After a few hills, you will pass two entrances to Fort Williams Park. The second one is the main entrance (watch for turning traffic). Continue on Shore Road, which becomes Cottage Road after re-entering South Portland. Pass a cemetery on your right, then drop steeply down Meeting House Hill, bearing right at a busy intersection to stay on Cottage Road. Proceed straight on Cottage Road, crossing Broadway, then turning left on Hinckley Drive to arrive back at your starting point.

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Turn onto Highland Avenue from Ocean Street  (Google Maps)
Outer Highland Avenue on the approach 
to Pleasant Hill Road  (Google Maps)
Scarborough Marsh from Black Point Road  (Google Maps)
Turn onto Rt 77 from Black Point Road (Google Maps)
Rt 77 just before the entrance to Crescent Beach State Park (Google Maps)
View from Shore Road (Google Maps)
Entrance to Fort Williams Park (Google Maps)
Intersection of Cottage Road and Broadway (Google Maps)