Ryan Sherman is a guy you notice. Be it his eye-catching long red mane, ever-topped with a trucker hat, or that he may have struck up a conversation with you at one of his favorite Hamptons haunts, there’s just something very “welcome wagon” about this Springs native. “I’ve got the gift of gab,” he laughs, which is probably why his interview-centric podcast, “Highly Educated,” has been such a hit. But this is Sherman’s superpower: the ability to connect and a keen knack for tapping into the rattle and hum of what’s around him. It’s made his company, the energetic marketing and branding firm Three Mile Media, a quick success since he founded it in 2023. A drummer in his free time, Sherman’s boundless warts-and-all love for the East End makes him a pretty great guy to know for local recs. Here are a few of his favorite things.
Favorite place to see music
Stephen Talkhouse (161 Main St., Amagansett, 631-267-3117) because it’s an institution. Some of my favorite concerts I’ve ever seen in my life have been in that venue. You can see some of the world’s most exciting acts and upcoming acts in an intimate setting, and that’s rare. You can’t normally see Marcus King in a place with 100 people. That doesn’t happen when he’s selling out [arenas], you know what I mean? That makes it 10 times more magical. And the bartenders and the staff? They’re the best.
Favorite local band
Local Motion from Westhampton Beach. I like those boys. They’re an exciting young group. They bring a lot of energy and play a lot around the Hamptons in the summer.
Favorite place to get pizza
Sausages Pizza (781 Montauk Highway, Montauk, 631-668-1144). It’s the best pizza in the Hamptons. I’m not scared to say that! I will go toe to toe. They’ve got the best buffalo chicken slice on Earth. They use a sesame crust. The owners, Hunter [Kelsey] and [his mom], Barb [Schultz], are amazing people.
Favorite place to see art
Lucore Art Gallery (87 S. Euclid Ave., Montauk), which is owned by Chris Lucore. He’s one of the nicest people I’ve ever met. He’s always hosting local shows [and] getting local artists involved. Also, Ashawagh Hall (780 Springs Fireplace Road, Springs) because I love the community aspect. I host my annual Bonac Print Shop Art Show there. This will be its fourth year.
Favorite old-school Hamptons business
One Stop Market (299 Springs Fireplace Road, Springs, 631-324-6055). It’s just an institution. My father’s ordered an egg sandwich there every Sunday since I was born.
Favorite restaurant
The Dock (482 W. Lake Dr., Montauk, 631-668-9778). It’s the Alamo of Montauk. The last beacon of localism in the town. Chris [Watson] runs that place like a Swiss watch, with the freshest seafood that you’re going to eat on Earth. Simple, homestyle dishes, fair pricing and camaraderie. It’s a place that you’re going to see good people, good families and some grumpy fishermen.
Favorite place to grab a beer
Rowdy Hall (177 Main St., Amagansett, 631-324-8555) because it’s warm and inviting, it’s cozy and they have a great beer selection.
Favorite thing about living in your hometown
All the woods and the beaches and just the beauty of nature here never ceases to amaze me. At the end of the day, the community changes. Families and friends move out and it becomes more unfamiliar by the year. The nature is what continues to make it familiar and to provide that vessel of home for us. I think that’s kind of really important to hold on to.
