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

Unlike many of its coastal cousins to the north, Old Saybrook, Connecticut is a worthy fall destination for history, food, and seaside views.

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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.


Scenes from Old Saybrook, CT in autumn.

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.

Old Saybrook's Historical Society and Church Green

Old Saybrook is home to 15 National Register sites.

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.


Fort Saybrook Monument Park.

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.

Old Saybrook ShorelineTwo 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.


Walt’s Food Market.

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.

Penny Lane Pub

Head to the Penny Lane Pub for traditional English fare.

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 2nd Saturday of the month.

Have you ever visited Old Saybrook, Connecticut in the fall?

This post was first published in 2013 and has been updated.

  • Moved from Brimfield, MA to Knollwood in Old Saybrook in August of 1958. Graduated from Old Saybrook High School, Class of 1959. Have many pleasant memories of the town and surrounding areas. Met my wife from Cornfield Point and married in the Congregational Church, Moved to Virginia in 1982 due to job transfer. I return to Old Saybrook for visits and class reunions. I love it!

  • I have seen the best of the best and it is always a pleasure to return home to Old Saybrook!!

  • Lived there just a few years when I was 4 and 5 years old, 1952-53. Moved a town up and spent a good amount of time in Old Saybrook. I have now lived in Chester for 25 years or so and frequent Old Saybrook. It has evolved to a terrific shoreline town has a lot to offer visitors. I have the good fortune of living near enough to enjoy this beautiful Connecticut town. The annual Main Street Chili Fest is awesome!!!

  • My God, look at these notes, we all grew up there, moved away and are homesick seeking ways to return. I was a southern city boy, who when we moved and rented there in 1959 had a bedroom overlook the Sound from Knollwood Beach. Found heaven and realized it when it was gone.

  • I lived in os for 10 of the most important years of my life. I wish I could have raised my 3 boys in such an invioriment as os

  • Judy, I know what you mean. Moved away from there last year at this time and have been wanting to go back. I will find a way no matter what. That is where I just want to be. Good luck to you.

  • im looking for a small farm in connecticut can anyone help im from michigan

  • I love o.s. I used to live there for about 12 years. I was from Clinton. I was born in New Haven, And I lived in Old Saybrook as a little girl. Then moved there when I got older. I miss the ocean a lot. I have been here in Kansas for about 8 years now. Left o.s. to come here for my husbands family. My husband Wayne was from New London. He died July 22nd 2012. Now I am trying to find a way to get back to o.s. Judy


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