Connecticut River Valley Road

Scenic road chapters

Waypoint introductions and full write-ups

1. 1. Old Saybrook

   Planning note

   Old Saybrook is where the day begins. Next is Essex.

2. 2. Essex

   Essex is the kind of Connecticut river town that makes visitors suspect it has been arranged for their benefit. It sits on the west bank of the Connecticut River, a few kilometres from Long Island Sound, and its main street runs down to a waterfront crowded with sailboats, cruisers and old brick warehouses. It was a shipbuilding village from the seventeen hundreds, and the Oliver Cromwell, a frigate of the Continental Navy, was launched here in 1776. The Griswold Inn, which opened the same year, still serves meals in a tavern full of ship paintings and old guns, and it is possibly the oldest continuously operating inn in the country.

   Read the complete Essex write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Essex comes up about 8 km into the recorded legs. Next is Chester.

3. 3. Chester

   Chester is one of those Connecticut River towns that seems too small to have so much going for it. It sits on the west bank of the lower river, in the hills of Middlesex County, a few miles up from the Sound, and has a tidy village centre with a handful of good restaurants, a couple of galleries and a tiny theatre. It is a fraction of the size of East Haddam across the water, and quieter, which is why riders like it.

   Read the complete Chester write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   about 19 km into the recorded legs you reach Chester. Next is East Haddam.

4. 4. East Haddam

   East Haddam is the town on the Connecticut River that most people know from the postcard: a long white bridge, a hillside of old houses, and a gothic opera house standing right at the water. The Goodspeed Opera House, built in 1876 by a local shipping and banking magnate, is a Victorian jewel, and it has become known as a home for musical theatre. Its tall wooden frontage faces the river like a stage set, and from the swing bridge, you get the best view. The bridge itself is an old steel swing span, and it still swings open for taller boats when needed, so you might sit in a short queue.

   Read the complete East Haddam write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   East Haddam, late in the day. Next is Middletown.

5. 5. Middletown

   Planning note

   Finish at Middletown. That is the ride.