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Old Saybrook, Connecticut | 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.

street-scapeI 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 GreenA 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-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.

waltsHaving 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 PubFrom 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” (Yankee Magazine, March/April 2012) before getting back on the road and pointing the car toward home.

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.

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Brenda Darroch

Author:

Brenda Darroch

Biography:

Digital Editor Brenda Darroch creates and manages content for YankeeMagazine.com, YankeeFoliage.com, e-newsletters, and Yankee's search and social media initiatives. Follow Brenda Darroch on !
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6 Responses to Old Saybrook, Connecticut | A Historic Village on the Connecticut Shoreline

  1. GARY RUDE December 6, 2013 at 10:17 am #

    I LOVE O.S. MY HOME SWEET HOME

    • Judy December 13, 2013 at 8:20 pm #

      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

      • J. Smith November 20, 2014 at 6:56 pm #

        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.

  2. Pat Z. December 10, 2013 at 9:35 pm #

    “There’s no place like home, there’s no place like home.”

  3. ann scourtes January 9, 2014 at 6:36 pm #

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

  4. Dennis November 21, 2014 at 9:09 pm #

    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

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