Old Saybrook, Connecticut in Autumn | A Historic Village on the Connecticut Shoreline

With the Connecticut River twisting alongside it, feathering its briny fingers through the eastern border before pushing into the Long Island Sound, Old Saybrook, Connecticut, is the ideal summer destination for visitors making their annual pilgrimage to the shoreline. Yet, unlike many of its coastal cousins to the north, this popular seaside town doesn’t shutter its shops and go into hibernation after temperatures drop and the last of the leaves flutter to the ground.

I headed down to explore Old Saybrook during that stretch of late autumn when midday drapes itself in shadows and pumpkins topped with witch hats jostle for space alongside streamers bearing tidings of comfort and joy. What I found was a town which tips its hat to the area’s historic roots on almost every street corner. It houses 15 National Register sites within its borders, and markers dedicated to parceling out slices of the area’s past sprinkle the landscape.

A quick jaunt down Main Street leads to the Old Saybrook Historical Society which encompasses the General William Hart House, Frank Stevensen Archives and historic garden. They weren’t open when I was there, so be sure to check their hours of operation before planning a visit. Cross the street and you’ll land next to a triangular patch of grass ringed by regal, historic homes and majestic churches. One of the two-legged markers that rise up from the turf proclaims this the Church Green—once home to the Third Meetinghouse.

More historical tidbits await curious minds at Fort Saybrook Monument Park, situated at the mouth of the Connecticut River and just a short drive down Route 154 from the center of town. Scattered throughout the park, which is open year-round at no cost to the public, you’ll find storyboards to  guide you through the village’s history. The park also envelops over six acres of marshland, and a wood-planked overlook allows bird lovers an easy vantage point from which to watch great blue herons, snowy egrets, and terns in their natural habitat. And, of course, there are sweeping, panoramic views of the Long Island Sound. Two active lighthouses—the Breakwater Lighthouse and the Lynde Point Lighthouse—still serve as the waterway equivalent of traffic lights around the Sound. And if the stubby Breakwater beacon looks vaguely familiar, you’ve undoubtedly passed many a car in Connecticut sporting its likeness on license plates—the proceeds from which go to preserving the Sound.

Having explored the waterfront, I turned and headed back to the shops and restaurants that line up along Main Street. In this eclectic swirl of independently owned businesses, the local barber shop and small town grocery rub shoulders with upscale artisan galleries and antique shops. What a perfect spot to indulge in a bit of retail therapy while taking care of weekly errands.

From sandwich shops to oyster bars, food options are abundant and cater to all preferences. But if you want to relax after a day of exploring and shopping, I suggest taking Yankee’s advice and popping into Penny Lane Pub to enjoy “English style fare and a neighborhood atmosphere” before getting back on the road and pointing the car toward home. Note: When planning a visit to Old Saybrook, Connecticut, in December, don’t miss the annual Christmas Torchlight Parade, generally held on the 2ndSaturday of the month. Have you ever visited Old Saybrook, Connecticut, in the fall? This post was first published in 2013 and has been updated.