Today I decided to head north on the Airline Trail starting from where I had turned around back in 2023 and ride up to Pomfret. I didn't get started until late afternoon but it was nice and sunny and not brutally hot (for a change!).
At The Start
I started in the middle of nowhere near Chaplin. The reason? This spot was close to where I rode to and turned around on a previous airline trail ride back in 2023. Details >
The former New York & New England Railroad ROW through Southbury, CT is now the Larkin Bridal Trail. This is a great trail!
The Ride
After a railroad-history-filled morning riding the trolleys trails of Woodbury and Middlebury, topped off with a delicious lunch washed down with a double IPA - I was still aching to do more railroad-history-related bike riding.
Next stop was the Larkin Trail. I took a look at the entrance on Rt 63 across from the Hop Brook Park and didn't see the ROW so I went to the Allerton Farms entrance instead. In order to satisfy my curiosity, I biked back to Rt 63 and saw that the ROW did end there - but it was cut off up high. Apparently as Rt 63 was modernized, it removed a lot of the embankment.
Well the ride was a blast - the Trail is very scenic and you ride thru quite a few rock cuts. The eastern section is nicer to ride because it is now mostly single track. The far western end of the trail feels like basically just a wide dirt road.
Allerton Farms entrance looking west
The other way takes you back to Rt 63
Beautiful tree canopy and super picturesque ROW
Man - I love riding thru rock cuts
Abutment - Remnants of the RR Bridge here
(South Street)
Ah - rock cut...
Ooo yeah... another rock cut
Thru marshland near the airport
A picturesque spot - note collapsed structure on right
Power Lines crossing
End of the (official) trail
Yep I t looks like it keeps gong
Parking at the end of the (official) trail
I headed from back here...
There is even a roller for mountain bikers
Of course I had to do it!
Highlights of the Trail
Two Minute Riding Video
History
This trail’s railroad history began in 1881 with completion of the New York & New England Railroad (NY&NE) between western Connecticut and New York. Following NY&NE bankruptcy in 1894, the New York, New Haven & Hartford Railroad (NYNH&H) took over the line until 1939.
Southbury, CT- 1892
New York & New England Railroad
The line was abandoned between Waterbury and Southbury in 1939 and from Hawleyville Junction to Southbury in 1948. The line between Hawleyville and Waterbury had one the region’s steepest grades up to Towantic summit. The severity of that grade is the key reason why the NYNH&H decided to upgrade and double track the alternative longer route from Danbury to Hartford via Derby Jct. in 1908-1911 and allowed this shorter route via Towantic to fade into insignificance.
The Southbury Station was up on the top of Depot Hill. It was razed during the construction of Interstate 84.
The final regular passenger service disappeared in 1932, and by 1937 most of the line east of Southbury was abandoned. The Hawleyville-Southbury portion existed a bit longer but was abandoned in 1948.
The Bridle Trail
The ROW was purchased by a Dr. Charles L. Larkin when the NYNH&H pulled out in 1939, and converted to a bridle path. Larkin was a wealthy Middlebury resident and horse lover and had land abutting the NY&NE ROW near South St. in Middlebury. He gifted it to the state in 1943 for a bridle trail.
I started in East Hampton - a quaint little New England town and I first grabbed a sandwich at the restaurant right at the trail head (it was delicious!).
East Hampton Trailhead
EastHampton was nicknamed Belltown for the 30 Bell Companies in town during the railroad's heyday
Below are enlargements from the lovely signage above - showing the railroad's presence in the town.
The Bike Ride
After the short climb and switch back descent over a bridge - the trail reaches the woods
One of many rock cuts
I started riding at exactly 12 noon and after a short bit, I rode thru a seemingly endless rock cut that was 10 to 15 degrees cooler. I was cold and thought I dressed wrong for the ride... but once thru the cut, it was warmer again.
A bit further up is apparently a more "official"starting point. There's a cranberry bog on the left.
The Official Trailhead!
The trail was really wide - loose gravel and dirt the whole way - a bit bouncy at times but never worrisome enough to pop a tire on a road bike.
The elevation chart shows about 400 feet change (about 1400 ft of total up and downs!) but it was a rail trail so the climbs were long gradual slogs - it was tiring but exhilirating at the same time!
See Willimantic map enlargement below as well
Although this was a rail trail and somewhat monotonous compared to mountain biking, there are a variety of scenic changes to make it interesting. You ride by ponds, cranberry bogs, fields, marshes, etc. At one point I almost ran over a snake!
Nice stonework
Finally, a railroad tie
All along the trail there are many offshoots
- great for exploring on a mountain bike!
The now filled-in viaducts were pretty impressive but probably more so in the winter or early spring when there isn't any foliage.
From the Spur Connection, North
Once past the Colchester spur connection you begin to see a lot more railroad ties scattered off to the side. IMHO its gets even prettier along this section. For a short stretch you even get to ride by a farm and see cows grazing - a welcome change from the usual green canopy of the deep woods.
Signage is good
Beautiful Marsh section
The Google map is NOT up to date. Instead of the rail ending at the south side of the Willmantic River, then you can continue on over a bridge and ride all the way to Bridge Street. You pass the Eastern CT Railroad Museum. This added another mile or so to the trip:
New bridge and extended trail
I had planned to stop in Willimantic for a snack but decided to turn around and head back instead. The ride back to the new bridge was interesting as the river is on your left and an old railroad yard and the railroad museum in on your right. Right at the bridge there is a connection to the Hop River Rail Trail as well so you could ride for days!!
This is the new bridge over the Willimantic River
Signage at the new bridge - the Hop River trail goes off the the right
The Connecticut Eastern RR Museum
Finally reached my (extended) destination - Bridge Street in Willimantic
The Colchester Spur
Once I reached the Colchester Connection, I headed south on the spur. What a bore! Don't waste your tine on this section - the only thing that kept me going was the chance to see the Colchester station(s).
When I arrived at Colchester, the railroad stations didn't disappoint! They were kept up nicely - the old freight station was a bike shop and the passenger station was a package store. Although I had a craving for a nice ice cream, I had to make do with a tall Yuengling instead!
I headed back up the Colchester Spur (yawn) and was happy to reconnect with the main trail - anxious at this point to finish up this trek. The ride back seemed to take an eternity as I was getting a little tired but the scenery was pleasant and the mileage good for me.
Check out a short video (2:26 minutes) of the ride
About the Railroad
"The Air Line" was envisioned as a direct route between New York City and Boston. Built to bypass the Shoreline Route east of New Haven Railroad, the Air Line at its completion connected to the New York, New Haven, and Hartford railroad at the Cedar Hill Yard in New Haven, CT, where it then continued on to Boston.
The Airline Route
"shortest distance between New York and Boston"
The Air Line route opened in 1873 and was 25 miles shorter than the Shore Line. In 1875, it was reorganized into the Boston and New York Air-Line Railroad, and later, the New York and New England Railroad (NY&NE).
One of the most memorable and most famous trains of the Air Line was the "Ghost Train." Created to attract wealthy travelers, the luxurious Pullman cars were painted white with gold trim, and the staff of the train wore white uniforms. The service started in 1891, but was short lived and ended in 1895.
After being bought by the New Haven in 1898, the NH upgraded the line by raising bridges and filling in the massive Lyman and Rapallo viaducts to handle heavier trains. Its amazing when you pan through an acme mapper topo and see just how many embankments were created.
New York-Boston through trains ended in 1924, and by 1937 most trains used the Shoreline, with the Air Line being used mainly for a few oversized and heavy freight trains. Sadly by 1964, the Portland to Willimantic segment was abandoned.
Be sure to visit this excellent site: abandonedrails.com to read more history details. The above texts were sourced and condensed from this site.
