This route can be done as a 6-day tour leaving directly from New York City, or it can be done as a 4-day tour by taking Metro North to New Haven and starting with Day 3 of the cue sheets.** We took a very long, scenic route to get to New Haven because we wanted a 6-day tour.
The first day is almost entirely on rail trails. The first night is in North Brewster at the Bel Aire Motel – nothing special, but we’ve been allowed to bring the bikes into the room. There’s a fairly decent restaurant directly across (very busy) Rte. 22.
The second day is a fairly hilly but scenic route through Western Connecticut. There are several hotels in New Haven. This route goes to the Marriott Courtyard on Whaley Ave. It’s near Yale and there are numerous restaurant choices.
The third day takes you to Deep River, on the Connecticut River. This is a scenic route that initially goes along the shore, then heads inland into the hills. There’s a very nice B & B – Riverwind Inn. You stay there 3 nights and do loop rides on the 4th & 5th days. There are many beautiful places to ride in this area. The first suggested loop takes you across the river to the Goodspeed Opera House, an historic jewel box of a theatre. You can arrange to take a guided tour. Then continue on to Gillette Castle for a tour of the gaudy but fascinating home of the 19th Century actor, William Gillette. After that, you go back across the river on a ferry and into Chester, where framemaker Richard Sachs has his shop. Then circle down to Old Saybrook. The second suggested loop takes you to Devil’s Hopyard State Park and Chapman Falls, then loops down to Old Lyme before returning to Deep River.
Finally, you return to New Haven for a Metro North train back to Grand Central Terminal.
**If you want to start in New Haven, come out of the station, turn R on Union St., BR onto Water St. (Rte. 1) which becomes Forbes Ave., then R on Woodward and follow the cue sheet from there.