Connecticut has a habit of keeping its old buildings busy, and some of the best examples are taverns that were feeding hungry travelers long before cars, phones, or even your great-grandparents came along. This list covers seven of them, from a Revolutionary-era inn on Essex’s Main Street to a riverside barge in Westport that dates to around 1840.
Every stop still serves a solid burger, and each one comes with fireplaces, old beams, wild stories, or water views that a newer restaurant simply cannot copy. Save this one for your next road trip, date night, or Sunday drive, because history tastes better with fries on the side.
1. The Griswold Inn, Essex, CT
Here is a fun fact to share at the table: the ceiling in the Griswold Inn’s Taproom is made of horsehair and oyster shells. That is not a typo.
The Taproom itself has quite the backstory. It was built in 1738 as the town’s first schoolhouse, then hauled to Main Street by oxen in 1801.
That same year, the main three-story inn was built by Richard Hayden, giving Essex a landmark that has been welcoming guests for roughly 250 years.
Walking through the rooms is part of the appeal. The walls are loaded with relics, paintings, and photos, so it often feels like a small museum that happens to serve lunch.
There is a fireplace, live music in the bar area, and seasonal decorations that make the holidays here especially festive.
The menu sticks to classic American comfort with some personality. Look for the burger, fish and chips with coleslaw, the signature clam chowder, prime rib, and vegetarian potato cakes.
Venison and chicken pot pie have also earned attention.
Families are welcome, with a kids’ menu and high chairs available. Reservations are recommended for brunch, lunch, and dinner, and free parking is available in a lot and on the street.
2. Captain Daniel Packer Inne, Mystic, CT
Back in 1754, a tavern went up on Water Street along the Mystic River. It is still there, and it is still serving dinner.
The Captain Daniel Packer Inne splits its personality in a smart way. Downstairs is an English-style pub with a lively bar area, exposed brick walls, authentic wood beams, a fireplace, and mantles.
Upstairs, the dining room takes a more refined approach for anyone planning a date night.
The captain’s burger is the pick for this list, a smoky, juicy option served with fries. Seafood fans have plenty to work with too, including calamari, a cold lobster roll, pan-seared scallops, fish and chips, and lobster mac and cheese.
The clam chowder has a loyal following of its own.
I would save this stop for a full Mystic day, since it sits right in the village and stays open from 11 AM to 10 PM every day. Live music adds some energy, and a kids’ menu keeps younger diners happy.
Saturday evenings get busy, so reservations are a good idea for dinner. Parking options include free and paid lots plus street spaces.
3. J Timothy’s Taverne, Plainville, CT
Wings are the headliner in Plainville, but the building gets top billing for history. For nearly two centuries, from 1789 to 1979, this was Cooks Tavern.
The name changed to J Timothy’s Taverne in 1988, and the rustic, homey character stuck around. A fireplace, old woodwork, and a relaxed sports-bar energy make it an easy fit for game nights and family dinners alike.
The house specialty is “dirt” wings, which are fried, sauced, and then finished again for extra crunch. Honey BBQ is a popular flavor.
Burger fans can choose from juicy beef options or a black bean burger, and the menu also covers New England classics, a Buffalo chicken Cobb, and French onion soup.
This is a practical pick for groups. There is a free parking lot with plenty of space, a kids’ menu, and prices that typically run about $20 to $30 per person.
One planning note: the tavern is closed on Mondays, and there is usually a wait, especially on Saturday afternoons and evenings. Reservations help.
4. G.W. Tavern, Washington Depot, CT
A brook runs right behind the dining room. That alone makes G.W.
Tavern a scenic stop in the Litchfield Hills.
The building dates from 1850 and has a historic, cozy look inside, complete with a hearth for cooler months. When the weather cooperates, the patio puts you closer to the water, and dogs are welcome outside.
The menu is upscale tavern fare. The tavern burger and fish and chips cover the classics, while branzino and filet mignon are there if you feel like dressing up dinner.
Crab cakes, sweet potato fries, chicken pot pie, fried chicken, and a grilled chicken sandwich round things out, and the appetizers are worth a look before the main event.
This is the kind of place I would pair with a fall foliage drive through Washington and the surrounding towns. Prices generally land around $20 to $30 per person.
Check the calendar before you go. The tavern is closed Tuesdays and Wednesdays, and dinner reservations are recommended, particularly for Friday, Saturday, and Sunday evenings.
5. Old Riverton Inn and The Royal Coachman Tavern, Riverton, CT
Stagecoach travelers once stopped at this 18th-century inn in the quiet village of Riverton. Today, the draw is a burger with onion rings stacked right inside it.
That would be the Jesse Ives Bacon Burger, the highlight of the menu at The Royal Coachman Tavern. It is big, and it is the reason many people make the drive into this corner of northwestern Connecticut.
The tavern itself has a circa-1940s bar, so the inn mixes two eras under one roof. A fireplace, traditional guest rooms, and a calm, unhurried setting give it a classic country inn character.
The goat cheese and beet salad is a lighter option if someone in your group wants a break from comfort food.
Dogs are allowed, which makes it a friendly stop for road trippers traveling with a pup. Outdoor seating, a kids’ menu, and free parking add to the convenience.
Hours are limited, so plan ahead. The tavern is closed Monday and Tuesday, opens at 4 PM on Wednesday and Thursday, and serves from noon on weekends.
6. Black Duck Cafe, Westport, CT
Most taverns sit on solid ground. The Black Duck Cafe sits on a barge from around 1840, floating on the Saugatuck River.
It has been a Westport staple since 1978, known for its casual, family-owned spirit and river views. Live music and sports on TV keep things lively, and the outdoor seating is the spot to grab on a nice day.
Burgers are a strong reason to stop. The Black Duck cheeseburger with fries is a favorite, and the stuffed burgers get plenty of attention too.
Beyond burgers, the menu covers stuffed quahog clams, crab cakes, po boys, homemade soups, and award-winning duck buffalo wings.
Night owls, take note. The kitchen offers late-night food, and Thursday through Saturday the doors stay open until 12:30 AM.
Sunday brings brunch starting at 11:30 AM.
Prices usually run about $20 to $30 per person, and parking is generally easy with free and paid options nearby. Weekend evenings are the busiest stretch.
7. Oxford House Tavern, Oxford, CT
Locally owned and family run, Oxford House Tavern brings everyday dinner plans into a building with deep roots. It sits inside the historic Oxford House on Oxford Road.
The dining room and bar date to the 1800s and carry the charm of an old New England inn. There is also a small side room for private events, which makes it handy for birthdays and small gatherings.
A fireplace and live music add to the appeal.
The Tavern Burger is the signature here, and the beet salad makes a good partner for it. The menu covers comfort food, small plates, vegetarian options, and brunch, so it works for a quick lunch or a longer dinner.
Hours are generous, running until 10 PM most nights and 11 PM on Fridays and Saturdays. The kitchen closes an hour before posted closing time, so arrive early if you are hungry.
Families get a kids’ menu and high chairs, and there is plenty of free parking. Saturday evening is the busiest time to visit.
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