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.
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.
Historic Charm
The Deacon Timothy Pratt Bed and Breakfast is one of the oldest homes in the area, dating back to 1746. The inn has retained all of its colonial elegance while still offering modern luxuries such as in-room Jacuzzis. If you book the romance package for your stay, you’ll find chocolate truffles and a bottle of champagne waiting for you in your room. The staff is also happy to arrange in-room massages for couples or singles, and each room (from $225) is equipped with a fireplace to ensure maximum comfort and a romantic ambiance on cold winter nights.
When I arrive at the inn, I am offered complimentary port wine. I enjoy my aperitif while warming up in front of the parlor fireplace as two other guests play a competitive game of chess in another corner of the room. Breakfast the next day is served on fine china and consists of home baked goods, fruit and yogurt (egg dishes are added on weekend mornings). I inquire if the inn has hosted any famous guests recently. “We get people from all over,” innkeeper Connie Corbett tells me, “From Europe, Russia, and quite a few from New York. And maybe they’re famous…you never know!” Of the couple that recently visited from Russia, Corbett said “instead of having the port wine at dinner, they had it for breakfast.”
Where to Eat
Next door to the bed and breakfast is another colonial-era structure, listed on the National Register of Historic Places and formerly known as the James Soda Fountain. Anna Louise James, the first African American pharmacist in the state of Connecticut, ran the soda fountain from 1917 until 1967. Since then, the space has been used by various eateries such as a Juice Bar, Cafe and even Mediterranean food market and café, which mixed Moroccan spices and teas with sodas and ice cream as a nod to the soda fountain’s storied past. Now, it’s back to it’s ice cream roots, with the James Pharmacy, a gelateria and 3-room B&B mash-up.
For the best sea-to-table fare in Old Saybrook head to Main Street’s sustainable eatery Aspen for a fine-dining experience. Or choose no-frills Johnny Ad’s for simple options like lobster rolls, crab and calamari. Another option is Penny Lane Pub which provides a relaxed atmosphere for dinner or drinks with live music on Thursday, Friday and Saturday nights.
For an excellent cup of coffee, there’s the Paperback Café which also offers a full breakfast and lunch menu every day.
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. If staying at the Deacon Timothy Pratt Bed and Breakfast, call to arrange for free transportation from the train station to the inn.
Go to visitoldsaybrookct.com for information on upcoming events and things to do in Old Saybrook, CT.
Photo: Elizabeth Rose, Paperback Cafe
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram