Home: 12 Hours in Sag Harbor

Holidays at The American Hotel on Main Street in Sag Harbor. Michael Heller photo

Most year-round residents will scatter at some point during the winter months to exotic beach destinations, ski resorts or family getaways to Disney World. But for those forced to remain on the East End, for whatever reason, fear not. Sag Harbor is a world-class destination in itself. Here’s how we would spend 12 hours in the village with some of our favorite local gems.

A gingerbread latte at SagTown. Gavin Menu photo

8 a.m. – Coffee with a Holiday Twist

Sag Harbor is gifted with several unique coffee and tea shops, but we like to stop by SagTown Coffee on Main Street where the drinks are always kept seasonal. This year try a gingerbread latte, made with two shots of Nizza espresso, steamed almond milk, a pump of gingerbread syrup, whipped cream and a crumbled gingerbread cookie. Yum.

9 a.m. – Hike it Off at Long Pond

While this may be the season for overindulgence, there are many ways to walk off some of the festive meals you’ve enjoyed. One of our favorites is in the Long Pond Greenbelt, a collection of ponds, woodlands and trails that stretches from Sag Harbor to Sagaponack. The preserve is home to one the largest collections of rare species in all of New York State, and if you take your time you may be able to spot some of the rarer ones, like spotted turtles, tiger salamanders and least terns, as well as more common animals like white-tailed deer, box turtles and red-tailed hawks. We’ve even spotted mature bald eagles flying overhead and immature eagles fishing in Long Pond.

The network of well-marked trails is easily accessed from a trail head adjacent to Mashashimuet Park, near the Friends of the Long Pond Greenbelt’s headquarters off the Bridgehampton-Sag Harbor Turnpike, or behind the South Fork Natural History Museum, also on the turnpike.

The Express breakfast taco at Estia’s Little Kitchen. Courtesy photo

10 a.m. – Big Breakfast at a Little Kitchen

One of our favorite breakfast stops in Sag Harbor is conveniently close to the Long Pond hike, so we will stop off at Estia’s Little Kitchen on the Sag Harbor-Bridgehampton Turnpike, where chef Colin Ambrose and his team serve some of the best Mexican-inspired food around. Some of the dishes, such as George’s Ranch, Den Den’s Eye Opener, Isabelle’s Request and A’s Pop Bowl, have stories behind them so be sure to read closely. You can also ask for the Express Breakfast Taco special, scrambled eggs on two corn tortillas with mixed vegetables, jack cheese, salsa and bacon for a special price of just $12.50 through the New Year.

“Red Velvet Keys” by John Morfis, 2018, oil on panel, 9 x 7 inches

11 a.m. – Soak Up Some Culture

Sag Harbor is known for its arts and cultural institutions, from the Sag Harbor Whaling & Historical Museum to the south on up to Main Street, which is chock full of art galleries. This holiday season we plan to stop by the Grenning Gallery on Washington Street for its “Gems” show featuring works from Sarah Lamb, Ben Fenske, Marc Dalessio, Nelson H. White, Maryann Lucas, and others.

1 p.m. — Lunch and a Drink Fireside

Baron’s Cove has a storied past as a local meeting spot and watering hole. John Steinbeck and his buddies met there regularly to swap stories and hatch plans for the Old Whaler’s Festival, a precursor to HarborFest. Following a major renovation and the re-birth of the bar and restaurant, Baron’s Cove once again is a gathering place for the community and during the winter months we like to enjoy lunch or drinks fireside. At Baron’s Cove you can do that both inside the bar room and outside on the deck.

2:30 p.m. – Stroll to the Sea

Warmed up from your lunch by the fire, a trip to Sag Harbor is not complete without a walk to the end of Long Wharf. The views in winter are devoid of the crowds of boats and yachts that clutter the waterfront during the summer months. Bundle up, sit on the bench at the end of the wharf and take in a deep breath. As you head back to town, a tour down Main Street is a must. Sag Harbor is still home to many mom-and-pop businesses like the Wharf Shop, the Variety Store, In Home, Harbor Books and many others.

3 p.m. – Stop by the Library and Step Back in History

The John Jermain Memorial Library, named for the grandfather of Sag Harbor’s great benefactor, Margaret Olivia Slocum Sage, is one of Sag Harbor’s architectural and intellectual treasures. Stop by the historic building to check out not just books, but also art exhibits, lectures, cooking demonstrations, fitness activities and holiday celebrations. Also worth seeing is a stunning glass rotunda on a majestic second floor that was restored during the library’s recent renovation project.

The oversized backgammon table at The American Hotel. Gavin Menu photo

5 p.m. Happy Hour and a Bite to Eat at the Hotel

Where can you find one of the best happy hour menus in town, an award-winning wine list, a moose head on the wall and an oversized backgammon table? The American Hotel is not your average bar, and nor should it be for your special day in Sag Harbor. The happy hour menu, served from 4 to 6 p.m., is extensive and includes classic French onion soup, bacon and grilled cheese sandwiches, regular and crab cake burgers and a jumbo shrimp cocktail to die for. Grab a drink and a game at the backgammon table and watch the afternoon hours slip by.

7 p.m. –  Some Tunes and a Laugh at Bay Street

Bay Street Theater is a cultural institution in Sag Harbor and is known for its world-class Main Stage summer season, but its doors do not close during the winter months. Live music, comedy and even theatrical productions continue with an event just about every weekend. Check out baystreet.org for a complete schedule and close out your day with some live entertainment.