We Went There: Sag Harbor

Here's a fun fact for you: I wrote my college application essays about John Steinbeck. And to be completely honest, also spent the majority of my high school years obsessed with his writing. I mean, look at those eyes. #teendream

Now that you know how much of a nerd I was in high school, you can imagine that when I discovered there was a beachy Hamptons resort that combined my love of dogs and my love of John Steinbeck, I was 500% in.

Baron's Cove in Sag Harbor bills itself as an all-American waterfront resort with an impressive history of hosting names like Jackson Pollock, Paul Newman, Truman Capote, and Kurt Vonnegut. And, frequent guest John Steinbeck actually began his great American road trip with his dog Charley (documented in  Travels with Charley) at Baron's Cove. To celebrate this little piece of literary history, the resort offers a dog-friendly Travels with Charley Package that we had the privilege of trying out this summer.* 

The Travels with Charley Package came with some great perks, including a free copy of Travels with Charley, a comfy bed for Dave, dog dishes, waste bags, a Baron's Cove frisbee, and a special pup cookie. It also included a restaurant credit for humans in the beautifully renovated resort restaurant.

Read on for our recommendations for a pup escape to Sag Harbor.

Eat and Drink: 

Puppy Picnics: For dog owners, Sag Harbor's many waterfront picnic tables mean it's easy-peasy to dine with your dog. Pick up some pizza at Conca D'Oro Pizzeria or get some froyo at BuddhaBerry for alfresco/al-Fido meals.

Caffeinate: Get your morning buzz at Grindstone Coffee and Donuts. And donut forget to come hungry. (Sorry, couldn't help it.) But I mean, look at these.

Beachy Burgers: LT Burgers has some of the best diner food downtown—which is evidenced by the A-list autographs all over their walls. Stop by for a giant burger, boozy milkshake, or delicious kale salad. 


Explore Downtown Sag Harbor: Downtown Sag Harbor is everything you expect a town in the Hamptons to be—preppy couples in pastels, expensive cars, and carefully-curated galleries. Walk up Main Street for the people watching or pick up your next read at Harbor Books.

Make a splash: Escape to a local beach or just paddle around in Baron's Cove's luxurious saltwater pool. Although dogs are not allowed in the immediate pool area, they are allowed in the common seating outside the fenced pool zone.

Rock the Night Away: One of the best parts of Baron's Cove is it's luxurious porch of rocking chairs. Grab a cocktail and watch the sunset over some calamari or bang bang shrimp

Salty Dog: We love Foster Memorial Beach for woof-friendly walks. Enjoy the sea views or play a game of Fido frisbee on the sand.

Getting There:

You can get to Sag Harbor from Midtown Manhattan via the Jitney's Montauk Line. Pets are allowed in D.O.T. approved carriers for an additional fee of $10.


I've already talked about how much we loved our stay at Baron's Cove, but you can learn more about rates and packages at their website. Also, here's their dog policy.


Do you love Sag Harbor? Have you been there with a dog? Tell us what we missed.

xo Heather


*We received a free stay at Baron's Cove in exchange for our Instagram posts, but this blog post is not sponsored.