This Connecticut Town Has The Most Walkable Downtown
As a compact town laced by wide sidewalks that break out into narrow winding lanes in between the buildings, downtown Chester has walkability at its core. The streets of downtown Chester are adorned with historic buildings from its beginnings as a shipbuilding and mill town which today house locally owned boutiques, galleries displaying the works of local artists, and one-of-a-kind eateries serving food for every palette. Places like Chester Gallery which operates inside of an 1860 farmhouse or the Little House Brewing Company which occupies a building close to 200 years old are mere steps away from the parking lot or if you are staying longer, your accommodations.
Arriving in Chester
Chester is only two hours from New York City and Boston with ample parking opportunities downtown. Parking is available along Main Street, with additional public parking located on nearby Water Street and Maple Street, and overflow parking available at Laurel Hill Cemetery during busy times.
Alternatively, if you plan on spending more than a day in Chester, the Millhouse Downtown Chester has the capacity to accommodate five guests. The apartment takes up 1,000 square feet of space on the ground floor of a renovated 200-year-old Millhouse. The space has since been restored and is equipped with self-catering facilities or alternatively Chester’s restaurants, as well as everything else downtown, is within a minute’s walk of the front door. The apartment, like many other homes in town has incorporated Pattaconk Brook into its landscape with a waterfall in the back yard and Adirondack chairs for sitting on.
Mill and Shipbuilding History
It will not take you long to notice that a lot of the businesses in Chester are housed inside of historic buildings. This is because Chester has a background as a former mill town. To learn more about the town’s past, the Chester Museum at the Mill, as its name would suggest, is located at an 1860s mill site which overlooks a waterfall. The museum is just mere steps from the center of Chester, granting free admission to two levels of award winning permanent and seasonal displays.
Although the first settlers arrived in 1692, Chester was not incorporated until 1836. Soon after the first settlers arrived, they established permanent homes and many mills were erected in town. As it is adjacent to the Connecticut River, the primary mode of transport was via boat, thus the shipbuilding industry became an important part of the town’s early history.
The first floor of the museum narrates the story of Chester’s 70 water-powered industries across 20 different sites on the two branches of the Pattaconk Brook which flows underneath Main Street and behind many of the shops and restaurants. The second floor of the museum features exhibits on the Wangunk People who were the original inhabitants of Chester, and another exhibit showcasing Chester’s fashion history.
An Arts Community
Chester is an established arts community, with several galleries in town such as the Chester Gallery, which is contained inside a restored farmhouse from 1860 and has seen the addition of a sculpture garden on the grounds. Exhibits change during the year but the quality of work from Connecticut artists remains the same. Their work appears in different mediums such as paintings, works on paper, sculptures, and baskets.
Additionally, the Norma Terris Theatre regularly develops exciting and original new musicals. As a developmental theatre the scenes, songs, and costumes change regularly based on audience’s reactions. However, the Terris Theatre is responsible for many new and reimagined musicals that have gone on to do runs on Broadway, off-Broadway, national tours and other regional theaters.
A Foodie's Paradise
There is a reason Chester is a go-to destination for foodies and that is because despite being a small town, it has a versatile selection of restaurants from breweries to fine dining spaces. Gran Arso serves authentic Italian cuisine with a menu that changes with the seasons and what local produce is available at the time of the year. To pair with your meal, there are local and world wines, locally brewed beer, and handcrafted signature cocktails that, much like their menu, also change with the seasons.
For a more laidback evening, or even just stop by for a couple of drinks before dinner, Little House Brewing is a favored spot in town for residents and visitors alike. Like many establishments in Chester, the Little House Brewery has had many prior occupations such as a meat market, post-office, barbershop, and bakery. Today it includes a taproom and tavern.
Exploring the Valley
Chester’s proximity to the Connecticut River makes it optimal for visiting other nearby towns in the valley. Just like Chester, the town of Essex has a history of its own, except this one is rooted to the railroad. The Essex Steam Train and Riverboat takes passengers on a ride through the Connecticut River Valley on a restored vintage steam locomotive.
Across the river from Chester, East Haddam serves as a starting point for exploring nearby state parks, including Machimoodus State Park, a 300-acre landscape of hiking trails and river-view overlooks. The area is great for birdwatching.
Further on the coast where the Connecticut River meets the Long Island Sound, Old Saybrook has a blend of outdoor and cultural activities, including its own theatre. The Katharine Hepburn Cultural Arts Center not only hosts arts programs on more than 300 days out of the year, but it also has a museum packed with personal letters and memorabilia from Katharine Hepburn’s career.
Connecticut's Most Walkable Downtown
Chester’s downtown lets you move through history, among former mills which now house a museum that preserves the town’s history and heritage and art galleries. The town itself makes for a peaceful walk; the brook flowing through town creates streams, ponds, and manmade waterfalls. Everything in town is so tightly wound together that all you need to get around is a good pair of walking shoes. Chester is truly a pedestrian town.
