Last Updated:      2008

Length:                Harborwalk; 2 3/4 miles

                             Hillside Trail; 1.2 miles

Difficulty:            Harborwalk; Easy. Flat paved trail.

                             Hillside Trail; Moderate. Paved trail but hilly.


From I-90, take the Ted Williams Tunnel towards Logan Airport.  Turn onto William F. McClellan Highway. Take the Bennington St exit and travel straight at the end of the ramp to Bennington St (east). Turn right onto Saratoga St (Route 145). Saratoga St becomes Main St. After passing "Entering Winthrop" sign, take first right onto Pleasant St (Route 145). When you reach Shirley St take a right. Follow Shirley St to Elliot St. Follow Elliot St around to the left. Take a right onto Taft Ave and follow over the causeway, where the parking lot is on the left. If you continue following the road it will bring you to the guard house at the treatment facilities entrance.

Deer Island is home to a state of the art wastewater treatment facility. The island was so-named in the 1600s because of the deer that had been chased there from the mainland by wolves. Over the years, this small island has served a variety of functions, starting during colonial days as a detention center for Native Americans. It later served as a quarantine station and hospital for immigrants, an asylum for the city's outcasts, a reformatory for juvenile delinquents, an orphanage, a prison and a military post. In the 1940s, the Army Corps of Engineers built a causeway connecting the island with the town of Winthrop. The treatment plant is surrounded by fencing, but a paved path takes you completely around the islands perimeter. The first half of the island also has paved trails traversing the inner hills, which afford some great views of the harbor and Boston. Also located in East Boston is the East Boston Greenway .

Starting from the map board next to the parking lot; You have several choices. You can take the Harborwalk Trail which traverses around the island, traveling in either direction and/or you can travel the Hillside Trail, which travels along the inner island. I traveled both by first riding the Harborwalk Trail and then the Hillside Trail after arriving back at the parking lot. However, a map board shows the many different loops possible, as well as, the many different access points.  Located along the trails are informational sign boards detailing various facts about the island and Boston Harbor.

Harborwalk: Facing the signboard, head right and cross the road to where the trail brings you along the shoreline. Great views of the planes landing at Logan Airport. At 0.4 miles the trail splits. Go either over a small hill or along the shoreline, as they both merge again on the other side of the hill. Another trail split on the other side of the hill. Left takes you across the road alongside the treatment facility while straight continues alongside the shoreline. They merge again near the guardhouse. You come to the pier at 0.9 miles where you have to navigate through security fencing. Another intersection at 1.2 miles. Straight simply bypasses the point, so head right to the islands southernmost point. A signboard here identifies all the other islands in the harbor. The trail then becomes cement as it follows the seawall on the opposite side of the island. You pass by the 140 foot high, 3 million gallon egg shaped digester tanks. Quite a sight. You come to a wide plaza and a Porto-potty at 1.7 miles. You come to the first of three trails that head up to the Hillside Trails from the Harborwalk at 2.2 miles. Continue along the shoreline as the trail is paved again with granite borders. You pass a second trail heading uphill and finally a third trail heading up. The trail heads around the bend back to the parking lot at 2 3/4  miles.

Hillside Trail: Facing the signboard, head right. Just before the trail crosses the road turn left up the Hillside Trail. You gradually climb the hill as it affords you a great view of the treatment plant. Stay straight at the intersection and reach the ridgeline. Turn right towards the tower and a vista at 1/2 mile. This vista is the highpoint and overlooks the treatment facility. Great views of the Boston skyline, as well as of planes landing at Logan Airport. The trail then heads down to the Harborwalk so, head back the way you came, but follow the top of the ridgeline. This will bring you to a second overlook, after which the trail goes down a steep incline and up to the last vista, which is a dead end at 0.9 miles. Note; all the side trails head down to the Harborwalk. This vista is called Shirley Gut and overlooks the parking lot and Point Shirley Beach which is located along the causeway. To return to the parking lot head back along the trail and take your first left down to the Harborwalk Trail. Take another left and this will bring you back to the parking lot for a 1.2 mile round trip.