3 Days in Hartford, Connecticut, from Historic Asylum Hill to Pratt Street’s Revival

There are two very different sides to Hartford, Connecticut: the “Insurance Capital of the World” and the thriving entertainment hub. This city isn’t all about business — it’s teeming with reasons to stay and play. What makes the city so charming is the way that old and new fuse together so seamlessly.

Victorian homes sit steps from modish restaurants. Longtime arts venues share the spotlight with the Yard Goats, the city’s much-loved Minor League Baseball team. And old haunts exist alongside booming modern-day breweries that put the city on beer enthusiasts’ maps.

Add to all that music events spanning everything from live performances along the riverfront to a long-standing annual jazz festival, and all of a sudden, three days may not feel like enough. But the good news is that the city’s many angles mean no two visits will feel exactly the same. Ahead, you’ll find some top picks that guarantee a fun-filled weekend in Hartford.

As always, check for travel guidelines and closures before planning your trip.

Friday: Embrace Downtown’s History

Start your day downtown with a pragel (pretzel + bagel) at G Café Bakery and enjoy them as you stroll through nearby Bushnell Park. The 37-acre green space includes sculptures, the two-tiered marble and stone Corning Fountain, a vintage carousel from 1914, the Connecticut State Capitol and the Museum of Connecticut History. The museum is free throughout the week, so take advantage before continuing your journey west to Asylum Hill, Hartford’s first suburb. There are a number of the original private homes still intact, like the gabled Gothic Revival Perkins-Clark House, which was built in 1861, near the corner of Woodland Street and Asylum Avenue.

Hartford has more than a few standout barbecue spots, so carve out time to stop at one of the best. Lunch at Black-Eyed Sally’s Southern Kitchen & Bar (the Asylum Street location) is always a good decision — the menu is peppered with sandwiches, brisket and the all-important sides. It’s the perfect spot to refuel before your main attraction of the day, the Mark Twain House & Museum. The author commissioned the High Victorian Gothic home and lived in the 11,500-square-foot space with his family from 1874 to 1891. Today it houses a museum and gorgeous gardens.

Take a break from the history lesson and head back downtown to Pratt Street, the best pre-dinner spot for pop-up shops and live music. Check the website to make sure you don’t miss any fun events while you’re in the area. Even if there isn’t anything official going on, the pedestrian-only street is lined with bars with outdoor seating. During baseball season, you’ll often find special pregame events with drink specials happening along the street.

When it comes time to dine, visit Sorella for wood-fired pizza and authentic Italian fare. Finish the day with a cocktail from L Bar, an airy spot with elevated takes on classic cocktails.

Saturday: Shop Local Wares and Taste Local Brews

On day two, you may need a strong cuppa to get moving, so make your way to Story and Soil Coffee on the edge of the Frog Hollow neighborhood, which puts you in the perfect position to start your epicurean tour of the city. A walk through Frog Hollow will reveal Latin American flavors, as it’s home to the city’s largest Colombian and Puerto Rican communities. Park Street is often referred to as “New England’s Spanish Main Street,” given the number of shops and restaurants owned by local families.

Start eating your way through the neighborhood: Sol de Borinquen Bakery prepares mouthwatering sugar doughnuts and Puerto Rican specialty snacks like tres leches cake and sorullos (corn fritters). For a great Cuban sandwich, pay a visit to Los Cubanitos Bakery. Antojitos Colombianos presents various empanadas, arepas (grilled cornmeal cakes) and tropical shakes that virtually transport you to Colombia.

After trying a little bit of everything on Park Street, it’s time to browse the shops on Pratt Street in the downtown neighborhood. Hartford Prints offers urban streetwear and unique letterpress stationery, and Morneault’s Stackpole Moore Tryon, a high-end clothing store that’s been around since 1909, is famed for dressing past presidents. Then make your way to West Hartford for a visit to the White Rabbit, an antique and vintage shop where you never know what treasures you’ll find.

Hartford is home to some great breweries and you’ll experience some of them on your second night. Start with bar bites and the ales at Thomas Hooker Brewery at Colt. The taproom serves up delectable bites like jerk mushroom tacos and chicken sliders that are perfect for a shareable supper. Next up, call a car and make your way north through downtown to City Steam Brewery for a tap list spanning house-made brews and guest beers — they also host comedy nights.

If you’re craving a late-night tipple, hop in a taxi for a five-minute drive to Little River Restoratives for swanky cocktails and punches served up in a moody brick-walled bar.

Sunday: Surround Yourself with Art, Sports and Music

Begin the day at a brunch spot you’re likely to see on Instagram, the Place 2 Be, known for its pancake board and bottomless mimosas. Follow up the meal with a visit to the Wadsworth Atheneum Museum of Art, which has more than 50,000 works ranging from sculptures and paintings to rotating exhibits. The museum also occasionally hosts demonstrations that accompany the exhibits, like glassblowers at work.

Once you’ve got your art fix, hop in the car for a visit to the Harriet Beecher Stowe Center. This was the home of Stowe, the author of “Uncle Tom’s Cabin,” and serves as a museum that encourages discussion around the social justice issues she tackled. For the full experience, make sure to take the guided tour.

Given Hartford’s year-round appeal, there is always something going on. Before your visit, explore the city’s festival and events calendar for any special itinerary items. For example, Bushnell Park hosts live music in the summer months, including New England’s largest free jazz festival in July, and the Riverfront is the site of Taste of the Caribbean & Jerk Festival in August. April through September, the Minor League Baseball team (delightfully named the Yard Goats) fill up the stands at Dunkin’ Park.

Wherever your afternoon takes you, make your way downtown for one last swanky feast at Raw (make sure to reserve a table). The interiors are part fancy and part edgy, and Raw’s menu reflects its name with an impressive raw bar. The coconut sake mussels and grilled whole prawns are a must, along with a variety of seafood entrées that offer a twist on beloved New England classics.

End the trip with some entertainment: You can never go wrong catching a show at The Bushnell, a performing arts center that hosts international comedians, concerts and musicals (past acts have included John Oliver and performances like “Wicked” and “Cinderella”). Once the curtains lower, take a 13-minute walk to Vaughan’s Public House for a Guinness nightcap — a wonderful end to your Hartford adventure.