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Old Saybrook in Connecticut for a Quick Weekend Getaway

A trip to the town of Old Saybrook, Connecticut is a trip back in time. Everyone loves a quick weekend getaway, whether it’s just across the water, or across town.

In NYC during the summer, those who are lucky enough flee the island for weekends at a time, overpopulating the Hamptons, and pissing off Montauk locals. But in the winter, not everyone has options anymore. For many, the chance to jump on the Jitney and head towards their share house no longer remains.

Others in the city go into hibernation during winter months. Singles try to pair off before the cold freeze. Couples get ready to hunker down to Netflix and chill, which when you’re married, or even engaged, actually means watching a movie and chilling.

Of course one of the most fun parts of winter, or any season, is escaping reality for a few days with a quick weekend getaway to somewhere unfamiliar and suitably different from normality.

Escape Reality With a Quick Weekend Getaway to Old Saybrook

A short ride on the Amtrak, or an even less expensive on the Metro North, as I later learned, will transport you into another world. It’s actually Old Saybrook, Connecticut, but this town, located between the Long Island Sound and the Connecticut River feels more like a journey back in time.

The Rabbit Hole in Old Saybrook - quick weekend getaway

Stop at the Rabbit Hole Tavern on your walk through town. It’s one of those aforementioned places where modernization occurred, but old school style remained.

Its central distance between NYC and Boston makes a quick weekend getaway to Old Saybrook an ideal short break destination. Not just for vacations, or short weekend getaways, but work conferences as well.

The nearby Saybrook Point Inn is a frequent meeting place for large work retreats from all over Boston and other surrounding U.S states.

Old Saybrook, Connecticut in Video

Explore this selection of videos taken from in and around the town of Old Saybrook in Connecticut. See why a trip to this small town in Connecticut is the quick weekend getaway that you really want to add to the short break bucket list this year.

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The Famous Residents of Old Saybrook

Much of the charm of this small, unassuming place resides in one of its most famous residents. Katherine Hepburn, who famously had a home in Fenwick, considered Saybrook her home. Her adoration for the town parallels that of a true native New Yorker.

One visit is sure to justify some of Hepburn’s feelings, and explain just what it is that makes this little Connecticut town so special. This winter, get a train ticket and head out of your home for a quick weekend getaway to Old Staybrook, into one that brings the charm. Here are a few ways it does that.

Things to Do During a Stay in Old Saybrook 

The Kate Museum. The actress Katherine Hepburn is a legend here, and this small cultural arts center is dedicated to their most famous local resident. The building houses a small, permanent gallery honoring the actress, as well as holding plays, shows, and other events.

The Kate Museum in Old Saybrook - quick weekend getaway

Experience The History of Staybrook. Many times when you go on a weekend getaway, you don’t necessarily care about the history of the place you’re going. When was the last time your Bed & Breakfast weekend found you taking a historical stroll along the street? This is not the case with a weekend in Old Saybrook. Because here, all the little parts of its history are in itself what makes up the town. For one, being the actual birthplace of Yale College, and historical district North Cove.

The Vintage Feel. Vintage signs and retro stores are not the exception here, they are a norm. From old school signage to the James Gallery Soda Fountain, history is everywhere. And while many storefronts have changed, (even Saybrook has to move with the times somewhat), much of that historical charm has still somehow alluded destruction. The soda shoppe, where you can pick up an ice cream, or egg cream was home to the Lane Pharmacy, and Anna Louise James, the first female African American pharmacist.

Have a Drink Down the Rabbit Hole. Stop at the Rabbit Hole Tavern on your walk through town. It’s one of those aforementioned places where modernization occurred, but old school style remained. While you could see how this place becomes a busy spot on a Saturday night, on a Sunday it’s quiet and subtle. How many New York City taverns can you say that about on a Sunday?

A Stop at Saybrook Point Inn. There are a few places within Old Saybrook where one can reside for the quick weekend getaway, all quaint and lovely. But none as picturesque or all encompassing as the Saybrook Point Inn. Located on the Waterfront, it consists of both the main house and surrounding townhouses where families can stay.

quick weekend getaway
A gorgeous marina is the backdrop to a bar, pool and Fresh Salt restaurant, where docking boaters can take out their gourmet dinners and bring them back to their respective floating homes.

And though the Inn is a desirable destination for all out of towners, its appeal doesn’t end there. Welcoming and accessible to all its neighbors, it’s within the locals that the true presence of Saybrook is felt.

This feature was contributed by Blake Mandelberg, a Native New Yorker , freelance writer and creator, EIC of Style Island, a daily Lifestyle Destination.

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Chris is an avid travel writer who enjoys exploring the globe and writing about his exciting travel experiences. Chris produces some of the in depth travel feature articles and interviews here at Gloholiday.

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