The Remington on Main Is Writing Chestertown's Next Great Restaurant Story
The welcoming entrance to The Remington on Main. Photo courtesy The Remington on Main.
Every great restaurant has a story. In Chestertown, the latest chapter began inside the historic Remington Building, where one of the town's most beloved dining rooms found new life—and a new identity.
Replacing a longtime local favorite is one of the toughest assignments in the Adirondacks. Regulars arrive with memories, favorite booths, and impossibly high expectations. That's exactly the challenge The Remington on Main inherited when it opened inside the historic Remington Building in downtown Chestertown.
The good news? Locals can relax. Better yet, visitors searching for memorable places to eat in the Adirondacks have another reason to make Chestertown part of their itinerary.
The Remington doesn't try to recreate what came before. Instead, it confidently establishes its own identity—one built on thoughtfully prepared food, genuinely warm hospitality, and the kind of atmosphere that encourages lingering over another cocktail or one more shared appetizer.
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Signature dishes take center stage.
Every restaurant has that dish people can't stop talking about. At The Remington, there isn't just one.
The crab cake arrives beautifully browned, with a crisp exterior giving way to generous lumps of sweet crab that need very little embellishment. It's the sort of appetizer that immediately answers the question, "Did we choose the right place?" The answer is yes.
Ahi tuna entree, perfectly prepared.
The ahi tuna is another standout. Perfectly seared and silky in the center, it balances freshness with bold seasoning without overwhelming the fish itself. It's a dish that feels equally at home in a coastal restaurant as it does in the southern Adirondacks.
Even a classic Caprese salad feels elevated. Ripe tomatoes, creamy mozzarella, prosciutto, fragrant basil, and a drizzle of balsamic create something refreshingly simple before the heartier courses arrive.
Then there are Forty's Wings.
They've quietly developed a following among locals for good reason. Crispy, generously coated, and packed with flavor, they're exactly the kind of appetizer that disappears faster than anyone planned.
For those craving something more substantial, the New York Strip delivers everything steak lovers hope for—a flavorful sear, tender interior, and careful execution that lets quality ingredients do the talking.
The nightly specials deserve equal attention. Rather than relying on the same predictable menu every evening, the kitchen gives diners a reason to come back regularly, and many do.
Hospitality that feels genuinely personal.
Excellent food may bring guests through the door once.
Hospitality is what brings them back.
The all-crab crabcake
One of The Remington's greatest strengths is that diners never feel like just another table. Owner involvement isn't hidden behind the scenes.
Guests are personally welcomed, checked on throughout the meal, and made to feel like they're visiting a favorite neighborhood gathering place rather than simply ordering dinner.
That level of attentiveness is becoming increasingly rare.
The service strikes a comfortable balance—professional without being formal, friendly without becoming intrusive. It creates the relaxed pace that makes Adirondack dining so appealing after a day hiking, paddling, golfing, or exploring nearby Gore Mountain and Lake George.
A historic building with new energy.
The Remington Building has long been part of Chestertown's story, making it a fitting home for a a restaurant that can match its personality.
Inside, the atmosphere feels polished without losing its Adirondack roots. The historic setting lends character that can't be manufactured, while the comfortable dining room invites everything from casual weeknight dinners to celebrations with family and friends.
The cocktail program deserves mention as well.
Whether beginning the evening with a handcrafted cocktail or ending it with one more drink after dessert (as long as you’re not driving), the bar has become a destination in its own right.
The Caprese salad.
ADK Taste recommendations.
When to go.
Weeknights offer a relaxed dining experience, while Friday and Saturday evenings bring a lively energy. Because The Remington does not take reservations, arriving shortly after opening at 4 pm—or dining earlier in the week—is often the best strategy, especially during summer and peak foliage season.
What to order.
Start with the crab cake (we’ve also had it as an entree) or Forty's Wings. Follow with the ahi tuna or the New York Strip, and always ask about the nightly specials. Save room for dessert. We devoured the flourless chocolate torte on our last visit.
Insider tips.
Street parking is generally easy throughout downtown Chestertown. During summer weekends, expect a short wait if arriving during peak dinner hours. Since reservations aren't available, flexibility pays off.
Pair it with.
The Remington pairs naturally with a day exploring Loon Lake, hiking nearby trails, shopping in Chestertown, or spending the afternoon at Gore Mountain before heading into town for dinner.
ADK Taste perspective.
Great Adirondack restaurants do more than feed people.
They become gathering places. They welcome travelers after long drives, celebrate anniversaries, host spontaneous Tuesday dinners, and slowly earn the trust of the communities around them.
That's exactly what appears to be happening at The Remington on Main.
Replacing a longtime favorite could have been an impossible task. Instead, The Remington chose a smarter path—not by chasing nostalgia, but by creating new traditions of its own.
For locals, it's become the kind of restaurant that's easy to recommend when friends ask where to eat. For visitors exploring Chestertown NY restaurants, it's one more reminder that some of the Adirondacks' best meals aren't always found in the largest resort towns.
Sometimes they're waiting in a historic building on Main Street, where the owner greets you at the door, the cocktails are thoughtfully crafted, and the hardest decision of the evening is whether to order the crab cake again—or finally try the special.
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