More Terrific Towns

Main street is the center of a city, the soul of a town and the heartbeat of a community. Here in Connecticut, centuries-old buildings share blocks with trendy restaurants and an art gallery is never too far away. And we’re fortunate to experience all four seasons, so Main Street in the summer can become a whole new place in the winter. Bottom line: it’s where you see old friends, support local businesses and truly become a part of where you live.

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Main Street, Ridgefield

Chester

A small town with a huge art scene, galleries and studios dot the Main Street landscape. All located within a half-mile stretch of road are Maple and Main Gallery, West Main Street Studio, Lori Warner Studio/Gallery, Dina Varano, Leif Nilsson Spring Street Studio & Gallery and Chester Gallery, in addition to clothing and gift boutiques and antique shops. Thankfully “look but don’t touch” doesn’t apply to the Main Street restaurants, which include standouts River Tavern, OTTO Pizza and Good Elephant Bistro. Stop into the Pattaconk for a beer.

Old Saybrook

Old Saybrook has long been known as the home of legendary actress Katharine Hepburn. Main Street in Old Saybrook is now known as the home of the Katharine Hepburn Cultural Arts Center, a 250-seat theater which abuts the town green. Just down the road is the General William Hart House, built 250 years ago with a second-floor view of the port where his ships were docked. As the Chamber of Commerce website states, “Main Street charm. Shoreline beauty.” Rounding out the eclectic mix of Main Street is Maximus Antiques’ 4,500-square-foot showroom, the Paperback Cafe, Liv’s Oyster Bar and the Penny Lane Pub.

Guilford

Whitfield Street, the main hub in this suburban, shoreline Shangri-La, runs along the west side of the Town Green. This area is classic New England and stakes its claim as the third-largest collection of historic homes in the six states. There’s a variety of eateries near the Green including Ballou’s Restaurant & Wine Bar, breakfast-and-lunch spot The Marketplace, and South Lane Bistro. Too stuffed to move? Stopping by independently owned Breakwater Books would be a novel idea.

Niantic

A seaside village in East Lyme, Niantic’s Main Street runs parallel to Long Island Sound. Take the kids or grandkids to the Children’s Museum of Southeastern Connecticut. Then, after the babysitter picks them up, head east. Stop by Lillian’s Cafe, Cafe SoL, Gumdrops & Lollipops Candy, Ice Cream & Diner, The Black Sheep, The Spice Club, or Skipper’s Restaurant for waterfront dining, drinking and desserting. Which reminds me. Don’t forget to pick up the children. (Get it? Deserting. OK, I’m done.)

Middletown

The National Trust for Historic Preservation called Middletown’s downtown one of America’s most romantic main streets. With well over 30 places to eat, drink and congregate, we’re falling in love too. The Buttonwood Tree offers art, music and open-mic nights, and there’s no shortage of clothing stores, gift shops, jewelers and boutiques. Frankly, it’s an embarrassment of riches for our small state’s 20th-most-populous city.

Ridgefield

This western town along the New York state line is no stranger to our biannual November best-towns issue and has eagerly adopted the moniker of “Connecticut’s No. 1 town.” Picturesque Main Street is one of the big reasons why. Historic: Keeler Tavern has a cannonball lodged in its siding from 1777’s Battle of Ridgefield. Unique: Aldrich Contemporary Art Museum is the only one of its kind in the state and has no permanent collection. Historic and unique: The Museum in the Streets is a 30-station, heritage discovery trail along Main Street.

Wallingford

Wallingford’s “main street” is essentially made up of two roads — the first block of North Main Street and Center Street down to Route 5. The restaurant epicenter is North Main, with Michael’s Trattoria, J. Christians and the Library Wine Bar & Bistro topping the menu. Heading west down the hill on Center Street brings you by Wallingford Flower Shoppe (2017 Best of CT florist), and numerous salons, boutiques and bars. When you get to the bottom of the hill, a quick right will bring you to Redscroll Records, another Best of CT winner and featured in our roundup of the state’s standout record labels on page 28.

Litchfield, CT

Litchfield

Where’s the center of it all in Litchfield? Very logically, it’s where North, South, East and West streets meet by the Litchfield Green. In such a historic town, it’s only fitting to visit the Litchfield History Museum, Litchfield County Jail (prisoners were held here during the War of 1812) and St. Michael’s Parish, which was completed in 1921 but contains stained-glass windows from a previous incarnation of the church from 1851. And speaking of fitting, R. Derwin Clothiers can help you achieve a modern look, in case you soaked up too much history.

Collinsville

This quaint village in Canton and national historic district is nestled in the crook of the Farmington River where abandoned factories and mills have been repopulated with local businesses. Approaching from the south, as soon as you take a right onto Bridge Street for the first time, you just get it. What a cool place. LaSalle Market and Lisa’s Crown & Hammer Pub, housed in an old train station, are small-town treasures. Want more small town? There’s horse-drawn carriage rides and yoga in the street.

Winsted

Going even farther into the Northwest Corner is the city of Winsted in the town of Winchester. This Main Street is home to Ralph Nader’s American Museum of Tort Law, the world’s first legal museum. Another unique establishment is Gilson Cafe and Cinema, a former vaudeville theater which is now a movie house with two screens and a built-in restaurant. And we can’t go to Main Street in Winsted without stopping at the Winsted Diner. As we wrote in our June diners feature, “This place captures the quirkiness, the local character, the old-fashioned authenticity that we look for.”

More Terrific Towns

Mike Wollschlager, editor and writer for Connecticut Magazine, was born and raised in Bristol and has lived in Farmington, Milford, Shelton and Wallingford. He was previously an assistant sports editor at the New Haven Register.