To say Sag Harbor is full of history and character is an understatement. You only have to start with the first chapter of Melville’s Moby Dick (in which it’s mentioned) and go from there. Soon, you will find yourself on a journey with whalers and sea captains, slaves and freemen on the Underground Railroad, Depression-era farmers, bootleggers and bohemians.
My childhood memories of Sag Harbor are of a charming but half-empty, half-rundown town you didn’t want to walk through at night. More recently, Sag Harbor has traded in its coveted “un-Hamptons” status for a more bustling “Heart of the Hamptons” vibe—a change that not all locals (myself included) are happy about. But among the pricey Madison Avenue boutiques and Manhattan-priced eateries that have popped up over the last five or so years are also a handful of mom-and-pop shops that have survived Sag Harbor’s ups and downs over nearly a century, as well as some exciting new places imbued with the friendly, casual and creative spirit of the old village.
This small hotel in the middle of Main Street was once the site of the execution of eleven Red Coat soldiers captured during the Revolutionary War, and their spirits are said to occasionally haunt the place. The building itself makes modern day visitors feel as if they’ve stepped back in time in a more friendly manner—from the gorgeous historic wallpaper and backgammon tables, to the wicker chairs on the covered porch and elegantly served meals.
With most of the rooms recently renovated, this hotel has the casual feel of a hip beach motel, with the addition of a swank new pool and main building that houses a restaurant looking onto the harbor and a bar and grill where the burgers are ace.
An on-site aquaponic “farm” adds to the excellent, locally-sourced menu. Friendly, knowledgeable waitstaff, outdoor seating, and a back room housing fishtanks and a grow wall of herbs and greens characterize this village staple.
Remember Dairy Queen? Bay Burger—a long walk or short bike ride out of the village proper—is reminiscent of those 1950s drive-in burger and malt joints. This time, however, the burgers are made with grass-fed beef and home-baked rolls, and there are seasonal local veggie sides. A fun atmosphere and outdoor seating is included with the homemade ice cream.
Situated on the Long Wharf, smack in the middle of ocean liner-like yachts, is a little shingle shack serving up the best fried clams, shrimp, lobster and flounder to go. You can call in an order, too, to avoid long lines, then pick-up your lunch or dinner and sit in Marine Park or at the end of the wharf and enjoy alfresco.
A small space full of charm and locally-sourced dinner, lunch and brunch, this little cottage on the Sag Harbor Turnpike also has a fantastic wine list and edible gardens. Brunch is wonderful, and one must be prepared to wait for a table.
The incredible, high-up views of the harbor and bridge, and entrees like halibut baked in parchment with sun-dried tomatoes, tatsoi and toasted Israeli couscous, make this restaurant on Water Street a hard place to get into, but it’s worth it if you can.
A relatively new addition to Main Street, Grindstone has quickly become a favorite stop amongst locals and summer peeps alike. I mean, brioche style donuts made on the premises with high quality ingredients, plus great coffee and a friendly staff? C’mon, people!
Tucked into Division Street, across from the watchcase factory condo, is a cheese monger extraordinaire. You will simple not find a better source for cheeses from around the world, as well as local cheeses, olives, and house made take-out food and baguette sandwiches. It’s like Montepulciano, County Cork, and Auvergne all came to the Hamptons.
It’s probably just as well that this little bakery is hidden in a shingle shack between Division Street and Rector Street because their muffins and breads are so incredibly good that they usually sell-out by afternoon. The gluten-free items are indistinguishable from the “regular” stuff.
A true New York bagel shop that has all the fixings and flavors, lox and spreads, as well as a full deli counter, coffee bar, and fresh squeezed OJ.
On the quiet residential corner of Division Street and Henry Street is this lovely market and eatery that serves rustic, simple fair. Perfect for breakfast, lunch, or take out.
Often referred to as the “American Legion,” this year-round restaurant actually just shares the building with the veteran’s hall. Good drinks and a nice beachy atmosphere are hallmarks of the bar. Enjoy a Stone Fruit Martini with Channing Daughters flowering basil & peach vermouth on Tuesday evenings from July 4th to Labor Day and you can hear the Sag Harbor Community Band play on the patio in true Americana style.
This French-inspired restaurant has expanded their outdoor seating as well as their outdoor bar area to include easy chairs, torches, and piped-out music. Smack in the middle of Main Street, you can people watch as you sip. The place gets a lively crowd on the weekends in summer.
The “other” burger place in town, this one is more expensive but also has a bigger menu. Have fun reading celebrity signatures on the subway tiles (hint: a certain Coldplay frontman is featured, if you can read his handwriting). Milk shakes are a favorite with kids, but adults can pony-up to the bar to watch hard-to-see European football games and enjoy creative cocktails and wine.
Housed in one of Sag Harbor’s oldest buildings (the creaky floors are fabulous), this old fashioned toy store is also a great stop for creative gifts and cards. The staff is super helpful, and the shop has been owned and managed by the same family for decades.
I’ve heard people say, “Without the Variety Store, Sag Harbor wouldn’t be Sag Harbor.” With the demise of the beloved movie theatre from a fire in December, this historic shop feels even more important than ever. Forgot your sunblock? Check. Craft glue? Yup. Fabric, knitting yarn, needles? Cleaning supplies? Those figgedy-thingys your kids can’t live without? There’s nothing this quintessential family owned five-and-dime doesn’t have.
For excellently-sourced whole foods, organic produce, herbs, vitamins and homeopathy—as well as delicious healthy lunches, juices, and breakfasts in the café—head to Provisions. The staff is also knowledgeable which, when you feel a bad cold coming on, is like a godsend!
This bookstore/cat café/tea room could fall under any category. But for now, let’s just say it’s my favorite place to hang out. There’s a great little gift section, a cozy kids’ corner, loads of books (of course), two playful cats named Swidgeon and Wu, and now a newly-installed Dobra Tea bar.
If you’re interested in history, or just want to see some of the coolest collections from the 17th to 19th centuries gathered under one roof, this museum is a must visit. The majestic Greek-revival building on Main Street’s elegant “Captain’s Row” gives off a heady vibe that is both hypnotic and buzzing with fascinating narrative.
At the top of Main Street is this large village park, with tennis courts, sports field and playground (about to go under renovation). But the best-kept secret is that the park is connected to the Long Pond Greenbelt trail—a unique 1,100-acre expanse of interconnected ponds, woods, and wetlands that stretches nine miles from Otter Pond in Noyac to Sagg Pond and the Atlantic Ocean shore in Sagaponack.
Known by locals as Long Beach, this stunning stretch of sand-and-pebble beach—actually a former sandbar connecting Noyac to North Haven—faces Peconic Bay, with Shelter Island and the North Fork on the horizon. There are lifeguards and a traditional ice cream truck that drives through. The water here warms up faster than the ocean, so it’s a good early-season place to enjoy swimming. Cars regularly pull up alongside the beach to watch the incredible sunsets.