The Travelers’ Field Guide to Connecticut
Discover Connecticut’s Hidden Gems and Unique Attractions
Explore Connecticut’s unique charm with cool, hidden, and unusual experiences. Uncover secret spots, quirky attractions, and offbeat adventures waiting to be discovered.
UPDATED JUNE 2025
Places to Eat and Drink In Connecticut
Connecticut’s food and drink scene is one of those things that just feels good. From roadside lobster shacks and old-school diners to family-run orchards and the kind of ice cream stands that draw a crowd every summer night. There’s wine country here too, plus cozy cafés, farm stands, and bakeries that make you wish you had more room in the car. Whether you’re grabbing a snack on the way to a hike or planning a special night out, you’ll find plenty to love—and even more to eat. Want to go a little deeper? Check out Connecticut Grown for farm-fresh picks, follow the CT Wine Trail, or head to the state’s tourism site for more local flavor.
Family-Friendly Favorites
From pancake houses with crayons on the table to pizza joints with room to roam, these spots serve up kid-approved meals and grown-up peace of mind. Easygoing, welcoming, and reliably delicious.
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Lyman Orchards – Middlefield, CT
Lyman Orchards blends fun, food, and farming with its pick-your-own fruit fields, bakery, and seasonal mazes. With something new each season, it’s a place families can return to again and again. The historic setting makes the apple pie taste even sweeter.
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Rein’s Deli – Vernon, CT
A Connecticut legend since 1972, Rein’s Deli serves up authentic New York-style Jewish comfort food in a lively, welcoming atmosphere. From crisp latkes to hot pastrami, their massive menu has something for everyone. It’s the kind of place where the pickles hit the table fast—and the memories last even longer.
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Shady Glen Dairy Bar – Manchester, CT
With its crispy cheese-topped burgers, retro booths, and house-made ice cream, Shady Glen has been a Manchester family favorite since 1948. A burger joint with heart, history, and heaps of flavor.
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Chip’s Family Restaurant – Orange, CT
A Connecticut staple since 1966, Chip’s Family Restaurant is known for its welcoming atmosphere, homemade comfort food, and one of the most impressive pancake menus around. With everything from classic buttermilk stacks to inventive seasonal specials, it’s a place where breakfast lovers of all ages feel right at home.
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Pop’s Family Restaurant – Milford, CT
A true local gem, Pop’s Family Restaurant in Milford serves up scratch-made diner favorites with a big helping of hospitality. Family-run and full of heart, it’s the kind of place you’ll want to come back to—maybe even tomorrow morning.
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Flanders Fish Market – East Lyme, CT
This East Lyme seafood staple is part restaurant, part market, and 100% family-friendly. Enjoy fresh-from-the-dock dishes like clam strips, fish tacos, or lobster rolls, either on the patio or packed to go. A casual favorite with serious local roots.
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The Place – Guilford, CT
An open-air seafood spot with fire-roasted clams, picnic tables, and tree stumps for seats, The Place has been a Guilford icon since 1971. It’s BYOB, no-frills, and all flavor—like a New England clambake that never lost its roots. Show up hungry, bring your own extras, and settle in for one of the best meals you’ll…
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Beardsley’s Cider Mill & Orchard – Shelton, CT
Old-fashioned charm meets fall flavors at this cider mill and apple farm in Shelton. Sip cider, snack on donuts, and stock up on heirloom apples during the autumn harvest season. A simple, tasty stop that feels like a slice of Connecticut tradition.
Roadside Classics
Pull over and grab a bite at some of Connecticut’s most iconic roadside stops—where nostalgia meets good eats. From vintage diners and drive-ins to old-school snack shacks, these casual spots are worth the detour.
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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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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.
Romantic & Refined
Whether it’s a candlelit table for two or a sunset view over the water, these restaurants bring the atmosphere—and the flavor. Expect artfully plated dishes, thoughtful wine lists, and all the makings of a memorable meal.
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Connecticut Garlic & Harvest Festival – Bethlehem, CT
Every October, the quiet town of Bethlehem fills with the smell of roasting garlic and the sounds of a good time. The Connecticut Garlic & Harvest Festival is a small-town favorite with big flavor—featuring food vendors, crafts, live music, and garlic in just about every form you can imagine.
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Mystic Outdoor Art Festival – Mystic, CT
Every August, the streets of Mystic fill with art, music, and a laid-back summer vibe. The Mystic Outdoor Art Festival features over 250 artists, hands-on activities for kids, and live performances—all set against the backdrop of this historic coastal town.
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Pumpkintown USA – Connecticut
A quirky fall favorite in East Hampton, Pumpkintown USA is home to a full cast of pumpkin-headed characters, a scenic hayride, and plenty of cider and donuts. Come back during the holidays for The Christmas Ride—when the Pumpkinheads deck the halls and keep the fun going through New Year’s.
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Durham Fair – Durham, CT
A Connecticut tradition since 1916, the Durham Fair brings four days of farm animals, live music, midway rides, and homemade treats to the heart of the state every September. It’s one of New England’s biggest agricultural fairs—with small-town charm to spare.
Wineries & Breweries
Sip your way through scenic vineyards, rustic taprooms, and laid-back tasting rooms across the state. Perfect for a casual afternoon or a weekend outing with friends—many spots also offer food trucks, live music, and cozy patios.
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Hammonasset Beach State Park – Connecticut
With nearly two miles of beach, Hammonasset is made for laid-back days. Walk the boardwalk, swim in the Sound, hunt for shells, or just stretch out in the sun. It’s a classic Connecticut beach trip—easy, breezy, and full of salty air.
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Appalachian National Scenic Trail – Connecticut Section
This stretch of the A.T. offers some of the most mellow miles on the trail—ideal for first-time backpackers or easygoing day hikes. Follow the Housatonic River through quiet woods, cross wooden footbridges, and stop in trail towns like Kent for a bite (or a second breakfast).
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Weir Farm National Historical Park – Connecticut
This easy loop takes you through forest, fields, and pastures, with glimpses of historic stone walls and the pink cottage that once served as an artist’s retreat. Peaceful and uncrowded, it’s a quiet walk through history.
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Quinebaug & Shetucket Rivers Valley National Heritage Corridor
Whether you’re strolling a rail trail or wandering past farm fields and forest edges, the corridor offers a glimpse of New England before sprawl. You’ll find quiet, uncrowded paths winding through some of the last undeveloped green spaces between Boston and D.C.—especially peaceful come early morning or late afternoon.
Sweet Spots
Got a sweet tooth? From ice cream stands and retro candy shops to artisan bakeries and chocolate makers, these are the places to treat yourself.
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Hammonasset Beach State Park – Connecticut
With nearly two miles of beach, Hammonasset is made for laid-back days. Walk the boardwalk, swim in the Sound, hunt for shells, or just stretch out in the sun. It’s a classic Connecticut beach trip—easy, breezy, and full of salty air.
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Appalachian National Scenic Trail – Connecticut Section
This stretch of the A.T. offers some of the most mellow miles on the trail—ideal for first-time backpackers or easygoing day hikes. Follow the Housatonic River through quiet woods, cross wooden footbridges, and stop in trail towns like Kent for a bite (or a second breakfast).
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Weir Farm National Historical Park – Connecticut
This easy loop takes you through forest, fields, and pastures, with glimpses of historic stone walls and the pink cottage that once served as an artist’s retreat. Peaceful and uncrowded, it’s a quiet walk through history.
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Quinebaug & Shetucket Rivers Valley National Heritage Corridor
Whether you’re strolling a rail trail or wandering past farm fields and forest edges, the corridor offers a glimpse of New England before sprawl. You’ll find quiet, uncrowded paths winding through some of the last undeveloped green spaces between Boston and D.C.—especially peaceful come early morning or late afternoon.