10 Unusual Massachusetts Restaurants That Turn A Meal Into A True Adventure
Massachusetts knows how to serve up more than just good food. I’ve eaten my way across this state, and some restaurants stick in my memory not just for what’s on the plate, but for the wild, wonderful places they call home.
From dining behind the bars of a converted jailhouse to watching chefs work their magic over a roaring, open flame, these spots turn every meal into an adventure.
Whether it’s a seaside shack with waves crashing outside or a historic inn whispering old stories through its walls, these unforgettable settings prove that where you eat can be just as thrilling as what you eat.
1. Clam Box of Ipswich — Ipswich
Driving past this place for the first time made me laugh out loud. The entire building looks like someone dropped a giant takeout container on Route 133 and decided to start frying clams inside it. Since the 1930s, this roadside marvel has been serving some of the crispiest, most legendary fried clams on the North Shore.
What makes it an adventure is the sheer boldness of the architecture. You’re literally eating inside a piece of packaging.
The clams are sweet, the bellies are plump, and every bite tastes like coastal Massachusetts history. Kids go wild for the novelty, and adults come back year after year for the nostalgia and the crunch.
2. CLINK. at The Liberty Hotel — Boston (Beacon Hill)
Eating dinner surrounded by iron bars and brick cells feels oddly freeing. This former Charles Street Jail has been transformed into one of Boston’s most talked-about dining experiences, and the history practically oozes from the walls. I sat in what used to be a cell block and ordered a steak that cost more than my first car payment.
The menu is sleek and modern, a sharp contrast to the gritty past of the building. You can still see the original jail architecture everywhere you look.
It’s a surreal mix of luxury and lockup, and that tension makes every course more memorable.
3. FiRE+iCE — Boston (Back Bay)
Picture this: you fill a bowl with raw steak, shrimp, peppers, noodles, and whatever sauce strikes your fancy, then hand it to a chef standing at a massive round grill. They toss it all together in front of you with theatrical flair, and minutes later you’re eating your own custom creation. I’ve been three times, and I’ve never made the same meal twice.
The energy in the room is contagious. Everyone’s watching, experimenting, and comparing bowls.
It’s part buffet, part cooking show, and entirely interactive.
4. Turner’s Seafood at Lyceum Hall — Salem
Salem’s haunted reputation isn’t just for tourists in pointy hats. This 1831 building has seen everything from lectures to séances, and now it serves some of the freshest lobster rolls and scallops you’ll find anywhere. I asked our server if she’d ever seen a ghost, and she just smiled and said the kitchen gets cold at weird times.
The seafood is top-tier, but the real thrill is eating in a place with so much eerie history. The architecture alone is worth the visit.
Every creak and shadow adds flavor to the experience.
5. Salem Cross Inn – Fireplace Feast — West Brookfield
Watching a massive hunk of prime rib slowly turn on a spit over an open fire is mesmerizing. On special Fireplace Feast nights, this 1705 farmhouse goes full colonial, with chowder bubbling in iron kettles and bread baking in the hearth. I felt like I’d time-traveled, minus the smallpox and bad hygiene.
The smell of wood smoke and roasting meat fills the entire room. Everything is cooked the way it would have been centuries ago, but the flavors are anything but old-fashioned.
It’s history you can taste, and it’s absolutely delicious.
6. Kowloon Restaurant — Saugus
This Route 1 landmark is a time capsule wrapped in bamboo and neon. The moment you step inside, you’re hit with tiki torches, pu-pu platters, and a vibe that screams 1950s Polynesian fever dream. I ordered the scorpion bowl just to say I did, and it arrived smoking and glowing like a science experiment.
The place is massive, with multiple dining rooms and a stage for live entertainment. Even as the area around it changes, Kowloon stays gloriously, unapologetically retro.
It’s kitschy, it’s fun, and it’s absolutely unforgettable.
7. Woodman’s of Essex — Essex
Eating at Woodman’s feels like biting into a piece of Massachusetts legend. This is where the fried clam was born over a century ago, and they’ve been perfecting the recipe ever since. I grabbed a seat at one of the outdoor picnic tables, cracked open a steamer, and watched seagulls circle overhead like they knew something I didn’t.
The atmosphere is casual, loud, and wonderfully chaotic. Families, tourists, and locals all crowd in for the same reason: the seafood is unbeatable.
It’s messy, it’s authentic, and it’s the real deal.
8. Steaming Tender — Palmer
Few things beat eating meatloaf while a freight train rumbles past your window. Set inside an 1884 train depot, this spot is a love letter to the golden age of rail travel. The walls are covered in old schedules, photos, and conductor hats, and the menu is pure comfort food done right.
Every time a train rolls by, the whole building hums with energy. It’s loud, it’s charming, and it’s deeply rooted in local history.
Bring your camera, bring your appetite, and maybe bring earplugs if you’re sensitive to whistles.
9. The Student Prince & The Fort — Springfield
Walking into this place feels like teleporting to a Bavarian beer hall without leaving New England. The walls are lined with steins, the menu is packed with schnitzels and sausages, and the energy is loud, warm, and welcoming. I ordered the sauerbraten and felt like I should be wearing lederhosen.
The space has been a Springfield landmark for decades, and locals treat it like a second home. Seasonal festivities turn the whole place into a party, complete with music and toasts.
It’s hearty, it’s festive, and it’s wonderfully over the top.
10. Bogie’s Place (behind jm Curley) — Boston (Downtown Crossing)
Finding this place is half the fun. You walk through what looks like a wig shop sign, climb a narrow staircase, and suddenly you’re in a dimly lit, vintage steakhouse that feels like a secret only cool people know about. I felt like I was breaking the rules just by sitting down.
The steaks are perfectly cooked, the cocktails are strong, and the whole vibe is effortlessly mysterious. There’s no flashy sign or loud marketing, just word of mouth and great food.
It’s a hidden gem in the truest sense.