Spending the perfect day in Sag Harbor

The iconic windmill in Sag Harbor. (Credit: Krysten Massa photos)

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History at every turn, delicious eats, funky shops — just across the Peconic Bay from the North Fork and Shelter Island, Sag Harbor holds all the ingredients for a magical day trip.

Here’s how to spend the perfect day there. 

Start your day with a jolt of coffee and a doughnut

Begin your Sag Harbor adventure at Grindstone Coffee & Donuts. Located on Main Street, the shop dishes up homemade brioche doughnuts, Stumptown coffee, teas and kombucha. If they have it (the flavors frequently change) you want the Nutella S’mores doughnut.

Brush up on your history

Stroll through the old whaling village taking in the historic homes and buildings until making your way to the Sag Harbor Whaling & Historical Museum. The small museum is packed to the brim with nautical gems.

Surround yourself with tranquility

After burying yourself in the past, head to Mashashimuet Park where you’ll find the Long Pond Greenbelt Trail, a 3.4 mile trail that will take past beautiful views of ponds and woodland. Try to stay quiet and spot the many birds that call the area home.

Order dessert first

Hungry yet? Head to LT Burger for lunch. Go ahead and order dessert first. With milkshake flavors like french toast, death by oreo and berry good, it would be a crime not to start your meal with a sweet treat. But save room for a burger. They’ve got a traditional with all the toppings as well as turkey burgers and even vegan and vegetarian options so everyone in your party will be happy.

Window shop

After lunch it’s time to window shop. Pop into Harbor Books and pick up a new read. You’ll have to resist the urge to sink into one of the comforty chairs or order a tea from their café — there’s many more boutiques to check out.

Vintage lovers should visit Ruby Beets, a jewel of shop that curates a collection of vintage furniture as well as locally made decor such as pottery. Whereas, youngsters or anyone young at heart can’t miss the old-fashioned toy store, Wharf Shop.

Dine at the farm

Dinner time means Page at 63 Main. Ask for a seat by their aquaponic farm. The restaurant grows its own produce using several on-site aquaponic systems that are cool to see in action and make for some delicious eats.

Make a night of it

Not quite ready to say goodbye to funky Sag Harbor? Tuck in for the night at The American Hotel. Rumor is the ghosts of Red Coat soldiers haunt the place, but so far the only breathtaking sights we’ve seen have been the sunsets. 

Off the Fork is a new feature on people, places and things that interest us outside of the North Fork. This week’s posts were made possible by Westhampton Beach Performing Arts Center.

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