CT – Roadside Classics
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Harry’s Place – Colchester, CT
A century-old roadside landmark, Harry’s Place in Colchester serves up juicy burgers, footlong dogs, and fried seafood with a side of history—and a whole lot of heart. Still family-run and proudly unchanged, it’s the kind of spot where the summer breeze, picnic tables, and hand-spun shakes bring everyone back year after year.
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Heibeck’s Stand – Wilton, CT
Serving roadside favorites with a twist since 1931, Heibeck’s Stand in Wilton is a local legend known for its loaded dogs, creative specials, and unforgettable ice cream. From classic burgers to beet tacos and bang bang shrimp, the menu is as fun and unexpected as the place itself.
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Super Duper Weenie – Fairfield, CT
Super Duper Weenie in Fairfield serves up flame-grilled dogs, homemade toppings, and fresh-cut fries with serious roadside soul—and a side of fun. From the original food truck to the nationally recognized shop, this place has earned its reputation one weenie at a time.
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Guida’s Restaurant – Middlefield, CT
Guida’s in Middlefield has been a Route 66 staple since 1946, serving up footlong hot dogs, chili cheese fries, and Gifford’s ice cream to generations of happy roadside diners. It’s the kind of place where everything’s made to order and nothing needs to change.
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Claudia’s Grinder Shop – Farmington, CT
Claudia’s in Farmington serves big, made-to-order grinders, house-made soups, and hometown charm in every bite. Don’t skip the Nancy Special.
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Blackie’s Hot Dog Stand – Cheshire, CT
Hot dogs, history, and one legendary relish—Blackie’s in Cheshire has been a roadside favorite since 1928, proudly family-run and delightfully unchanged. It’s the kind of place where the menu is simple, the birch beer is cold, and the memories are served up with every bite.