Hot dog, all around. Small fry. Raspberry lime rickey. Maybe a grilled cheese if I’m feeling extra—don’t sleep on Sully’s grilled cheese. Everyone’s got a go-to order for Sullivan’s Castle Island. For nearly 75 years, it’s been the unofficial nostalgia capital of South Boston—a place where memories are made with every crinkle fry.

My earliest memory? Going to the original Sully’s with my dad and brother—back when the building sat a little closer to the middle of Fort Independence. It was smaller, squarer, with a silver railing you could lean on while eating your meal. The smell of the ocean. Seagulls on stand-by. Ketchup-stained napkins flapping in the wind. Pure joy.

Lunch was always followed by a trip to the playground—swinging, sliding, and climbing on cement statues of monogrammed animals, until we were out of breath. Then a hike up the hill to peek at Fort Independence. Those massive green heavy doors were usually closed, and my dad would whisper that a giant lived inside. We believed him, of course. After that? A run down to the obelisk monument commemorating Donald McKay, legendary shipbuilder, near the fish pier—playing tag with Dad as he darted around the base and somehow vanished around each corner like a magician.

My dad’s love for Castle Island and Sully’s came from his dad, Jim Dahill, who passed it down to the next generation, like eye color. There’s a park named after my grandfather—James F. Dahill Harborview Park—tucked right behind Sully’s and leading down to the pier. Family history is literally rooted in Castle Island.

Me with my grandfather Jim and my brother Richie on O Street circa 1975

Sully’s is more than just a place to grab a hot dog—it’s part of the fabric of growing up here. Post-game hot dogs. Bike rides with your best friend, $5 in your pocket. Skipping rocks after lunch. A treat you earned, a place that felt like your own. People drive hours just to get in line, and here we are, lucky enough to have it in our backyard. We locals understand that it’s better to go on an overcast day than a sunny Saturday during the summer. Rookie move. 

Every spring, when Sullivan’s reopens after its winter break, it feels like the official start of the season. A rite of passage. In the spring of 2026, they’ll be celebrating 75 years of slinging hot dogs, fries, and ice cream to generations of families.

Sullivan’s was founded back in 1951 by Dan Sullivan, Sr., with a simple goal: serve quality food at a fair price to families enjoying the scenic 22-acre slice of heaven that is Castle Island. The current brick building (a replica of the officer’s quarters from the 1800s) has been standing since 1986, but the spirit of that original stand still lives on.  This year, Sullivan’s Castle Island has officially received an America’s Classics Award from the James Beard Foundation—one of the highest honors in the food world. This award is presented to locally owned establishments with “timeless appeal” that serve high-quality food and hold a special place in their community. And let’s be real—Sully’s is exactly that.

If you grew up around here, you’ve got at least one Sully’s memory—maybe a few dozen. Maybe you camped out in a sleeping bag during the Tall Ships in ’76 or you walked around Castle Island with your newborn for your first public outing last week for an ice cream cone. Whatever it is, we want to hear it. Let us know your favorite Sully’s moment in the comments or maybe a new tradition that you’ve started—we’ll be right there with you, reminiscing over a raspberry lime rickey.

My brother Richie pushing my sister Courtney around Castle Island circa 1976.

To celebrate the James Beard Award, Sullivan’s is hosting two parties in addition to teaming up with their neighbors at Castle Island Brewing to launch a brand-new limited-edition raspberry-lime lager called Rickey Business—a fizzy, fun nod to Sully’s signature summertime drink.  You can get all the details here! 

Send along any photos from Sullivan’s you’d like to share to [email protected] 

Check out our video with NBC10 Boston on How to Order at Sullivan’s!