Air Line Trail

East Hampton Connecticut
Air Line Trail State Park

Brief History

The Air Line Trail was originally built in 1870 as a railroad offering fashionable, and rapid transit from New York to Boston.   The trail runs today from East Hampton to Pomfret in two sections:  South – from East Hampton to Windham, and North – from Windham to Pomfret – in all, it’s 50 miles through the towns of East Hampton, Colchester, Hebron, Lebanon, Columbia, Windham, Chaplin, Hampton and Pomfret, with an extension to Putnam and Thompson.

Today the Air Line Trail in East Hampton attracts Walkers, Road Races, Hikers, Horseback Riders, Cross Country Skiing, and Nature Lovers from across the state of Connecticut looking  for the fresh air and panoramic views.

For runners looking to enjoy the trail,  the Parks & Recreation Departments of Hebron, Colchester, and East Hampton along with the State of CT Department of Energy and Environmental Protection host an Annual Air Line Trail Ghost Run.

Air Line Trail Extension

The Jonah Center has been advocating for the extension of the Air Line Trail through East Hampton and Portland to Middletown.  In December 2013, the Jonah Center in cooperation with the Town of Portland organized and presented a public presentation on the current situation and possibilities for extending the air line trail.  The presentation was attended by over 80 people.  Since that presentation, the Town of Portland has created an official Air Line Trail Steering Committee, allocated development funds, hired a consultant, created a site plan,  successfully negotiated an agreement with Eversource Energy to use a 2.3 mile section of the trail in Portland, and obtained a $686,000 Recreational Trails Grant from the State of Connecticut in early 2016. The actual construction work, by Dichello Construction of Farmington, began with a ground-breaking ceremony on October 28, 2017.

In the meantime, East Hampton has developed plans and received funding to continue the trail from Alden Crossing to Cobalt Road in Portland. Improving this trail segment (just east of Portland) will be somewhat delayed as that route passes through wetlands and there are drainage issues being addressed by the Army Corps of Engineers.

Detailed Summary

The Air Line Trail  takes its name from the imaginary line drawn from New York to Boston, through the “air” so to speak, to illustrate the shortest possible route between these two major east coast cities. Building a completely new rail line however proved economically infeasible so, for practical reasons, the “Air Line” as it came to be called, used existing rails from New York to New Haven and began its journey to the northeast from there. On its way to Boston, the Air Line overcame tremendous obstacles in Connecticut’s eastern highlands including ridges, valleys and of course, politics.

Construction began on the Air Line Trail back in the late 1860s and by 1870 the first construction milestone, track from New Haven to Middletown, Connecticut was celebrated. Three years later, in 1873, the Air Line Trail  was completed as far as Windham, CT.  This was an especially challenging run for the Air because of the landscape which demanded a winding or serpentine rail bed. Despite being limited to the technology of the day, tremendous cuts through the hillsides were accomplished in combination with equally massive “fills” in the valleys to keep the air rail bed at grade. Nowhere was this more apparent than at the expansive bridges, or viaducts, over Flat Brook and Dickenson Creek in East Hampton and Colchester respectively.  Only 1.2 miles from each other, these stream valleys were first crossed by lengthy bridges. The Rapallo viaduct needed 800 feet of length to cross Flat Brook, and the Lyman Viaduct, just to the east, needed 1,000 feet to span Dickenson Creek.

Further east, another entity laid the rails from Windham to the Connecticut border for the connection with Boston. Here a major obstacle for the Air Line Trail was the crossing of the Quinebaug River located in Putnam Connecticut.  But the construction was complete in August of 1872 and, within a year, the reality of the original plan had come to fruition.

Intermittent rail traffic for passengers built up until 1876 when the first dedicated passenger run was scheduled. But it could only be effective if it offered time savings from the pre-existing shoreline route.  Slowly, incrementally, time was trimmed from the Air Line travel schedule and by 1885, with an hour savings on the six hour coastal run from New York to Boston, the New England Limited was established. The success of the Limited led to the delivery of new luxury cars by the Pullman Company in 1891. These new cars, white in color and highlighted in gold trim, prompted the railroad to paint the balance of rail cars white and the legendary Ghost Train was born.

Successful businessmen and prominent citizens, including President Benjamin Harrison, rode this increasingly well known air line that had gained its name as it sped across Eastern Connecticut with its seemingly luminescent cars being easily recognized – especially at twilight.

As time marched onward to a new century, technology increased, railroad engines became faster, cars became longer and everything became heavier. The quaintness of the Air Line’s winding grades, and the weight restrictions of the spindly trestle bridges built for an earlier era of travel, began to show their limitations. As a result of these limits, traffic began to taper off. Though local runs and intermittent passenger trains continued to run along the line, passenger service of the Ghost Train era concluded on May 17, 1902 when service defaulted to the shore line rails.

Once the faster passenger trains moved to the shore, it was the slower freight trains and local passenger traffic that kept the rail line alive for many years afterwards.  In 1912, to accommodate growing weight requirements, the two viaducts were strengthened by filling out their form with 20 months worth of dumped sand, ultimately covered with cinders to stabilize its surface.  This work of 100 years ago provided the massive appearance we still see today.

Disastrous flooding of August, 1955 washed out critical bridge work in Putnam Connecticut precipitating a string of train cancellations and section closures that, in retrospect, systematically crippled the air line from ever regaining its usable status. The construction of the interstate highway throughout the 1960s sealed the fate of any future hope of rail bound traffic.

Today: The Air Line Trail  exists in two sections:  South – from East Hampton to Windham, and North – from Windham to Pomfret with the Thompson addition out beyond.

The south section measures 22 miles and, with East Hampton and Hebron leading the way, is the most utilized and improved.  This section is highlighted by the two tremendous viaducts, but nearly every increment offers locally favorite locations as the trail passes over streams with their requisite stone work, through state forests, past town parks, and along wildlife management areas.  From the footbridges trail users still enjoy sweeping views throughout the seasons. Today’s surface conditions vary from compacted earth and crushed rock to gravel and stone dust.

The northern section from Windham to Putnam measures 21 miles with an additional 6.6 miles existing in Thompson. Here the trail has been cut back to its original width, and gravel has been installed from the Massachusetts line south to Sand Dam road, and from the route 12, Mechanicsville parking lot, 1 mile north to the 395 overpass. The rest of the sections in Thompson have been rough graded and work is still in progress. Some sections still have the original rail ballast.

Gravel has been installed in Pomfret, from Pomfret Station located on Railroad street, south to Covell road.  Work is in progress from Covell road south to Brooklyn road.  The level section through Goodwin State Forest in Hampton provides a smooth and scenic run, and the southern end of the trail in Windham features a paved surface.

As surface improvements are being made, the various sections of the Air Line Trail State Park are combining to form one of the best greenways in all of Connecticut.


Air Line Trail Parking


Limited parking at 82 Middle Haddam Road.

East Hampton

Limited parking at Smith Street, 0.2 miles from the intersection with Flanders Road


Exit 16 off Route 2; Follow signs to commuter lot which abuts the trail

Large parking and information center for the Air Line Trail on Bull Hill Road about 0.3 mile north of intersection with River Road

Large area of parking on River Road 800 feet south of intersection with South Street

Pull off for a few cars along River Road 0.4 mile west of intersection of River Road and Route 149

Pull off for a few cars along Old Hartford Road 0.1 mile east of intersection with Jones Street


Pull off for a few cars along Old Colchester Road 300 feet north of Heron Hill Road

Large Parking Area along Church Street (Route 85) one half mile south of intersection with Route 207

Parking area along Lebanon Road (Route 207) 0.35 miles east of intersection with Route 85


Pull off for a few cars along Leonard Bridge Road 0.35 miles north of intersection with Tobacco Street

Pull off for a few cars along Chesbro Bridge Road 0.1 miles north of intersection with Tobacco Street

Pull off for a few cars on the west side of Route 87, about 250 feet north of Columbia/Lebanon town lines.  (This parking area is in Columbia)

Pull off for a few cars along Cook Hill Road 0.4 mile south of its intersection with Synagogue Road

  • Pull off for 1-2 cars along Kingsley Road 0.4 miles west of the Windham/Lebanon town line


Pull offs for a few cars at the intersection of Beaver Hill Road and Windham Road (Route 203) in northeast Windham

Large pull off parking area for the Air Line Trail at the intersection of Chewink and Lynch Roads


Potter Road 0.6 mile north of its intersection with Route 6 in Goodwin State Forest


18 car paved parking lot at Pomfret Station, 13 Railroad Avenue (off of Route 169)

Parking adjacent to the air line trail, in town owned paved parking lot, west side of Pomfret Town Office, 455 Mashamoquet Road (Route 44)

Parking available in rear of town owned paved parking lot at Pomfret Senior Center, 207 Mashamoquet Road (Route 44)


Large parking lot at 121 Riverside Drive, (Route 12, Mechanicsville) located at the southern end of the Air Line trail in Thompson

Pull off for a few cars at Air Line trail crossing, 388 Sand Dam Road

5 car parking lot, located at 662 East Thompson Road, near the junction of New Road

Explore the Air Line Trail Today!

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The Chatham Historical Society was established in 1963 and today operates a complex
which includes an 1840 one-room school house and a museum, opened in 2006.
The present museum houses artifacts and memorabilia
that tell the stories of East Hampton, Middle Haddam and Cobalt history.

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