Old Saybrook, one of the oldest towns on the Connecticut coast, has lured visitors over the years with its proximity to public beaches and conveniently located boat and yacht marinas, positioned where the Connecticut River meets the Long Island Sound. Not surprisingly, summer is the town’s busiest season. But warm weather pleasures aside, there’s plenty to do here year-round as I discovered during a recent visit.

As I stroll down Main Street with its quaint wrought iron lampposts adorned with cheerful wreaths, I hear none of the jarring sounds typical of larger cities. A pack of dog walkers and joggers pass me on the sidewalk and either flash a smile or raise a hand as a friendly gesture. Boutiques, galleries, antique stores, cafes and historic homes line either side of the thoroughfare that extends from the train station all the way down to the waterfront. My stay revealed Old Saybrook to be a relaxing respite from the fast-paced lifestyle of New York City.


New Haven

15 minutes to Main Street from Old Saybrook

Plan Trip

A Star of Stage and Screen

The town is very proud of its most famous former resident, legendary film and theater star Katharine Hepburn. In fact, the arts center that opened in 2009 in the former town hall space is named in her honor. The Katharine Hepburn Cultural Arts Center, or “The Kate” as locals call it, hosts theater and dance performances, film screenings, lectures and other events in addition to housing a small museum devoted to Hepburn’s life and career. The museum is open Tuesday through Friday from 10am to 4pm although it is possible to schedule a tour outside of these hours. Dedicated Hepburn fans can also visit Harbor Books on Main Street for a selection of books all about the luminary actress.

Bikes and Hikes

A very bicycle-friendly locale, the area has a 10-mile bike loop that takes you from the downtown area to the Saybrook Point Marina and meanders beside the Long Island Sound before curving back up north. If you prefer walking to cycling, the Fort Saybrook Monument Park has a mostly flat path that winds through the marsh and highlights details of Old Saybrook’s history via storyboards posted along the way.

How to Get There:

From New York City, take the Metro-North New Haven Line to New Haven and switch to a Shore Line East train to Old Saybrook.