Chester, Connecticut. Editorial credit: Joe Tabacca via Shutterstock.com

This Connecticut Main Street Feels Like A Movie Set

From the moment you step onto Main Street in the charming town of Chester, you will feel as though you have walked onto a picturesque movie set. The cobblestone streets and colorful buildings make the town seem magical. You will want to reach for your camera as you pass by historic buildings and cheerful storefronts that look as though they belong on the streets of Hollywood's most idyllic small towns, such as Stars Hollow. If you are visiting the town, spend the day on Chester's Main Street, where you can linger in coffee shops, browse through unique local shops, and admire the nearby beauty of the Connecticut River Valley, all while experiencing the movie-set quality of the town.

Historic Architecture

The Chester Museum at The Mill in Chester, Connecticut.
The Chester Museum at The Mill in Chester, Connecticut. Editorial credit: Rachel Rose Boucher via Shutterstock.com

One of the standout features of Chester's Main Street is the historic architecture. The town has a rich history dating back to its incorporation in 1836, with roots that extend back to the 1600s. The area was originally named after Chester, England, where some of the early settlers came from. Experience the town's past by walking down the cobblestones of Main Street and seeing the historic buildings lining the street. Visit some of the buildings, such as the Old Stone Store, which was originally built as a merchant store in 1809. There is also the iconic Chester House Hotel, built in 1840. The old hotel and tavern is known for their monumental columns.

One of the oldest buildings on Main Street is the Hough Tavern, originally a relay station on a stagecoach line. The building dates back to 1783 and was built in the Federal Style, a classical architectural style that emerged in the United States following the American Revolution. Common features of these buildings included a square or rectangular floor plan, elliptical fanlights over doors, and Palladian windows. The Chester Meeting House is another historic building in the Federal Style. It was initially a meeting house and is now a community space and a historic site of great importance to the town. Near the center of downtown on Main Street, there is also the Chester Museum at The Mill. The historic mill also serves as a museum open to the public during the summer months. Exploring all of the historic buildings on Chester's Main Street gives the street a picturesque quality that resembles a movie set.

Quaint Local Businesses

Parade in Chester, Connecticut.
Parade in Chester, Connecticut. Image credit Joe Tabacca via Shutterstock

Beyond its historic buildings, Chester's Main Street is also lined with colorful buildings that house quaint businesses, making the street feel even more like a magical movie set. Browse through the shops, and you are sure to find a souvenir to remember the town by. If you're looking for something new to wear, stop by Lark, a quaint boutique featuring stylish clothing and accessories, perfect for the fashion-conscious. Black Kat Leather is another unique store that focuses on handmade leather goods and local crafts. Just when you thought the shops in Chester could not get more dreamy, right off Main Street, there is a romance bookstore.

Montgomery & Taggert is located on Water Street and is the cutest, coziest bookstore. Romance lovers can enjoy browsing a wide range of romance novels and literary gifts. Although the bookstore primarily focuses on romance novels, it also features several subgenres, including science fiction, fantasy, and historical romance. From the quirky gift shops to the cozy bookshop, the quaint local businesses will make you believe you must have entered a movie with unparalleled small-town charm.

Charming Restaurants

Main Street Historic District, Manchester, Connecticut. Image credit John Phelan
Main Street Historic District, Manchester, Connecticut. Image credit John Phelan via Wikimedia Commons.

One of the other aspects of Chester that makes it feel like a movie set is Main Street's cute restaurants and cafes. Imagine a movie where people walk through downtown, talking, laughing, and sharing a good meal at a restaurant. This is what you can expect to find on Chester's Main Street.

One of the best restaurants to see is The Brushmill by the Waterfall. Eating here makes you feel as though you are having dinner in a movie with the scenic waterfall view. The menu features award-winning dishes and fresh, local ingredients. Another great restaurant is The Village Bistro. Here, you can enjoy locally and regionally sourced menu items with a European flair. The atmosphere of the restaurant is truly unique with its vintage decor and intimate library lounge. Dining here feels like stepping back into a bygone era. There are also many charming breweries on Main Street, including Little House Brewing Co., where you can grab a pint and enjoy craft beers in a relaxed setting.

Scenic Outdoor Spaces

View of Cedar Lake in Chester, Connecticut.
Cedar Lake in Chester, Connecticut. Editorial credit: Rachel Rose Boucher via Shutterstock.com

Being near the Connecticut River and the River Valley, Chester's Main Street's beautiful natural scenery adds to its charm, and the Cockaponset State Forest is not far from town. The stunning thicket of lush green woods would make an excellent backdrop for a film, adding to downtown Chester's appeal as a movie set. The forest offers numerous opportunities for hiking and scenic views, and the nearby Cedar Lake is another beautiful spot, ideal for swimming in the summertime. Strolling along Main Street downtown, you can enjoy the stunning views of these nearby natural spaces. If you have time, take a side quest to explore the Cockaponset State Forest or the nearby lake. The serene beauty of these places will make you glad you visited.

A Movie Set Experience in Chester

Movie sets can take place anywhere and be anything, and something that makes movie sets in a small town memorable is their Main Street. Chester's Main Street is certainly memorable with its cobblestone path, historic buildings, cute shops and restaurants, and its beautiful natural backdrop. From exploring quaint boutiques and the romance book store to stopping to eat beside a waterfall view, there is something for everyone to enjoy on Chester's Main Street. Take a trip to Chester and explore Main Street to feel like an extra in a movie. The small-town charm you will find there will create lasting memories.

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