Southern extensions

The trail as originally built ended next to a cranberry bog at Smith Street, east of the village center of East Hampton. The right of way remained intact and unused as far as the end of the active track in Portland; some sections were used for unofficial trails with poor trail surface and frequent washouts.^[5]

In 1999, a bridge over Muddy Gutter Brook west of downtown East Hampton was designed and built by cadets of the United States Coast Guard Academy under the supervision of William O'Neill, an adjunct professor of engineering at the academy and former state governor. Due to confusion as to which state agency had ownership of the stretch of land, the bridge was built without the necessary permissions; it was almost demolished, but allowed to remain due to a lease agreement with the town.^[6] On November 1, 2002, the state DEEP acquired an additional section of railbed in East Hampton from ConnDOT; however, the trail was not actually improved over the section.^[7]

In 2011, a 0.5-mile (0.80 km) extension from Smith Street to Watrous Street was completed. A further 0.1-mile (0.16 km) section (including a bridge over the Pocotopaug Creek) was completed in June 2012, bringing the trail to Main Street in downtown East Hampton. During construction, the original railroad bridge was found to have been buried in the embankment next to the right of way, forcing design changes to the trail.^[8]

Around that time, East Hampton and Portland began planning to extend the trail to downtown Portland, which would additionally provide a connection to Middletown over the Arrigoni Bridge.^[9] In January 2015, East Hampton received a $400,000 grant for Phase I, running 1.7 miles (2.7 km) from Main Street to Aldens Crossing; that section opened in 2017.^[10][11][12] A second $538,000 state grant, awarded in March 2016, funded the 1.5-mile (2.4 km) Phase II from Aldens Crossing to the town line at Depot Hill Road.^[13] Work on Phase II began in 2017.^[11] As of January 2019, phase II was complete except for a 1,500 feet (460 m) section through protected wetlands, which may require a boardwalk.^[14]

In June 2018, Phase I of the town-maintained portion of the trail in Portland, Connecticut opened to the public,^[2] extending from the East Hampton town line to the YCMA Camp Ingersoll, a distance of 2.3 miles (3.7 km). Unlike the rest of the trail, the 2.3-mile right-of-way in Portland is owned by Eversource Energy^[15]

In December 2015, the town approved an agreement with Eversource to allow the construction of a recreational trail on their property; a formal signing took place on January 20, 2016.^[5] On March 2, 2016, town voters approved the $172,000 acquisition of a 22-acre (8.9 ha) former quarry Middle Haddam Road to serve as the trailhead; this served as the 20% local match for potential state funding. An existing quarter-mile access road to the quarry leads north from the trailhead parking area to the rail trail. Later that month, the extension was allocated $686,000 in the same round of grants that funded the East Hampton Phase II. The section was originally expected to open around April 2017; several delays ultimately resulted in an October 2018 opening.^[13][16][14]

Further phases in Portland are planned but not yet funded. Phase II will reach downtown Portland and the Arrigoni bridge, largely over the original rail route but with some deviations parallel to roads.^[15] It may also include a trail parallel to the active P&W tracks in Portland and the purchase of the former train station.^[5] Following abandonment by the railroad in the 1960s, the remainder of the original Airline right-of-way in Portland reverted to private ownership by adjacent landowners and would need to be leased or acquired by the town prior to construction of Phase II. Phase III will attempt to create a trail north parallel to the Connecticut River to reach Riverfront Park, the fairgrounds, and ultimately Glastonbury.^[5]

Willimantic River to Bridge St. (CT 32)

This section has a wooden plank crossing over the Willimantic River, using the old bridge as support, then shortly after that it becomes pavement and intersects with the end of the Hop River Trail and has an info sign describing the history of both of the trails. Then it takes a S-turn next to the Eastern Connecticut Railroad History Museum. Then the trail follows the driveway of the building leading up to the trailhead, just 900 ft. away from Bridge St. This section can be very loud at times due to being less than 100 ft. away from the Providence and Worcester Railroad, an active freight railroad with a stop in Willimantic.

Route 66, Windham to South Brook Road, Hampton

This section has seen many upgrades in recent years. The section's first 1⁄4 mile (400 m) was paved as part of the US 6/Route 66 interchange reconstruction project. The state and the towns of Windham and Chaplin cleared, graded, installed signage, and put down a smooth stone-dust surface on this section of the trail. This included the construction of a trail bridge over Boulevard Road.

Abutment of the former Parker Road overpass, which collapsed onto the trail in May 2016

South Brook Road, Hampton to Lewis Road, Hampton

This section was cleared and graded by the National Guard in the mid-1990s. The surface was not finished and is still rough in sections and there are drainage issues in areas that sometimes flood the trail. There has not been much maintenance done on the trail in the last few years, so even the areas that were cleared have become somewhat grown in. Still, the trail is passable for hikers, equestrians, and mountain bikers. The town of Hampton and the DEEP have plans to add signage and finish the surface of the trail with stone dust. This work has not yet been started. An abandoned overpass that formerly carried Parker Road over the line collapsed in May 2016; the trail section was briefly closed during cleanup.

Lewis Road, Hampton to Wrights Crossing Road, Pomfret

This section is under construction by the DEEP, DOT, and town of Pomfret. The stretch from Lewis Road to Covell Road is currently being worked on to improve drainage and finish the surface. The trail is completed between Covell Road and Route 169, with a smooth stone-dust surface. The section from Route 169 to Wrights Crossing Road is essentially complete, with some drainage improvements planned.

Wrights Crossing Road, Pomfret to Kennedy Drive, Putnam

This section of the trail is completely undeveloped. It has not been cleared and is overgrown, with a rough surface, tree falls, and several wet areas with drainage problems. It is necessary to climb embankments to cross some roads where former bridges have been filled in. It is not really passable and must be done on foot if attempted. The DEEP and the towns of Pomfret and Putnam have plans to clear and improve this section as part of the next phase of trail improvements. Currently, a DOT state-hired contractor is improving this section, with a budget of $5.5 million. Two pedestrian bridges are proposed: a 100-foot span over Routes 169 and 44 at the old train depot and another on Needles Eye Road near the Audubon Center. Three box culverts on Holmes Road, Modock Road, and River Road are also proposed. Estimated completion is Fall 2020.