Hometown Spotlight- Chester, CT

Chester is a quaint and artistic town on the Connecticut shoreline. Just minutes from the Connecticut River and the Atlantic Ocean, there are numerous activities to do throughout each season in Chester. However, the town of Chester is small- and I mean small... I'm talking 'see the whole town from one standing spot' small. Let me walk you through the joys and glory of this small Connecticut town; the place where I was lucky to be raised.

Chester is definitely known for its various marvels of cuisine, artistic culture, and boutique shops you'll just have to stop into.

Explore Chester.

Chester CT small town

Local Annual Events

Starry Night Illumination

In light of Covid-19, Christopher Owens, otherwise known as "Star Man" in Chester, created handmade wooden stars dazzled with string lights placed all over the buildings downtown. The town features 152 twinkling stars hung all over main street to help spread celestial joy throughout the night. This starry night event was the first large scale public art show the town has ever seen. As local merchants have been burdened with the struggles Covid-19 has inevitably brought, the stars were created to help bring light to a dark time. Visitors can sponsor a star that has already been hung, and support small local businesses, or purchase a star to bring back to their home. Take a stroll through the town and immerse yourself in this magical winter wonderland.

The stars are illuminated and the town Christmas tree is lit on the first Friday of December every year. The tree and stars remain illuminated until the end of February.

Chester Farmers' Market

Chester features a Sunday Market throughout each summer beginning June 14th until October 11th from 10AM - 1PM located on Main Street. The weekly market brings the community together in a beautifully sustainable way and features and array of local vendors. The market includes fresh produce, meats, cheese, breads, and so much more. The main goal of the market is to remain local in order to help the farmers in the area. Main street is closed off during the time of the market, giving patrons the freedom to walk about the town (don't worry there's parking just outside the market). A local band fills your ears with amazing music as you shop and if you're tired, the town provides a bistro area so you can sit and take in the scenery.

My recommendations once you get here:

Grab a slice of pizza from Frank Andrews Mobile Kitchen and a beer from Little House Brewing Company. Pick out some flowers at the Hay House farm stand and make yourself a beautiful arrangement to take home.

Chester Farmer's Market

Winter Carnivale

The Carnivale in Chester happens every year in mid-February. Numerous local vendors post up on Main street to sell their goods to patrons from all around. This winter festival poses as an opportunity for Chester merchants to showcase their products in a fun and cheery winter-way. At the event, local professional ice carvers are chosen to compete in the Carnivale Ice Carving Competition. The ice carvers begin in the morning and finish during the day, then await for the voting results to come in from the visitors that noticed each one. Just a short walk up the hill from downtown, the Chester Hose Company hosts the Annual Chili Cook Off. Local restaurants and vendors make their best chili and give out samples all day long. The visitors vote on their favorite chili, and the winner is chosen at the end of the day. Just a small fee of $5 is donated at the door, then you're encouraged to become a chili connoisseur!

Ice Carvings in Chester CT

Four on the Fourth

People come from far and wide to participate in the Four on the Fourth in Chester (even I do it some years)! On the Fourth of July, Chester hosts a four mile race beginning in the early morning and into the early evening. Hundreds of participants run the course at their own speed and local organizations recruit people to run the race for sponsorship. Different organizations raise money for charitable causes and visitors have the opportunity to donate as well. If you're not much of a runner, the spectators are just as important! Head down to the center of town, grab a bite to eat, and cheer as the runners sprint by. At the end of the race, there's a huge celebration in town to honor those who have worked so tirelessly. Many people stop for a bite to eat at Simon's Marketplace, or skip the food and head straight to Little House and The Pattaconk Bar for a pint.

**Note some of these activities in town have been postponed or slightly altered to meet new Covid-19 protocols and standards. Check each website before you visit if you have your eye on a specific event!

Four on the Fourth Chester CT

Chester Fair

The Chester Fair has been held every summer since 1877. It began as merely a small gathering for townsfolk, but today, people flood in from all over the state to attend the fair. From August 23rd to the 25th, visitors can enjoy an array of live music and entertainment, carnival games, rides, food trucks, and various animal exhibits. One of the most well known events consists of the famous pig race. Visitors bet on their favorite pig and watch them run around the course. It is quite the sight to see. The fair is perfect for families looking to get out of the house and have some fun for the night. When I was younger, I loved to grab some powdered sugar covered fried dough and ride the ferris wheel with my sisters. Last year (summer 2020), the fair was cancelled due to Covid-19 so patrons are eager to get out during the summer of 2021!

Admission for the event is $8.00 per adult, $6.00 per senior citizen, and free for children under 12. If you're looking to come all three days, the three day pass is $21.00. There is free parking, but the rides cost extra (purchased when there).

First Fridays

First Fridays are a long existing event in Chester. First Fridays focus on showcasing famous art of the town through various gallery walks and boutique stores open to the public. Chester is home to world renowned artists including Sol Lewitt, famous artist, and Peter Good, designer and creator of the Whaler's Hockey logo. If you're interested in upscale jewelry stores, visit Dina Verano Gallery and Lori Warner Gallery. If you're looking for perfect gifts for family and friends (or yourself), visit Simon's Marketplace for a wide array of boutique products. Each of these stores are open daily for perusing. Be sure to grab takeout from one of the amazing restaurants downtown and sit outside to enjoy playful guitar music from Leif Nelsson of Spring Street Studio. As you listen to the music, take a stroll through the studio to see breathtaking paintings inspired by the landscape in Chester. First Fridays are a unique event happening only in Chester. Come enjoy the beauty of a small town every first friday of the month.

Obviously, don't forget your mask when visiting each of these stores- they will require you to step outside and put one on if you're not wearing one.


I know... what you've all been waiting for. Food stops in Chester are highly regarded for their quality, diversity, and for their farm-to-table locally sourced ingredients. If you're looking to cleanse and refresh your palate, you've stopped at the right place.

Breakfast of Champs

  1. The Villager- This little breakfast spot is perfect for your early morning egg sandwich and coffee cravings.

Best Lunch Spots

  1. Simon's Marketplace- my personal favorite lunch spot featuring a decadent array of sandwiches, soups, salads, and hot lunches. My recommendations: The Caprese sandwich, the Mayflower sandwich, and definitely buy a baguette while you're there- it never disappoints.

  2. The Wheatmarket- another spot for amazing soups and deli sandwiches. I recommend the Griffin sandwich, the potato salad, and the molasses cookies.

  3. Moravelas- great spot for a quick bite featuring pizza and subs. Try the French Fry Pizza; sounds weird I know, but I promise you it's amazing.

Bars and Brews

  1. The Pattaconk Bar and Grille- emphasis on the BAR part. Grab any craft cocktail, beer, or wine and sit at the bar. Order the wings too!

  2. Little House Brewery- Sit outside under the hops vines, choose a unique beer or cider, and purchase a freshly baked Chocolate Sea Salt Pretzel.

  3. Whole Harmony Tonic- A Botanical Boutique + Mocktail Bar with a focus on Plant Medicine.

Upscale Dinner Dining

  1. Grano Arso- known for their luxury $99 Royale Martini incorporating dry vermouth, citron and a cracker-style garnish atop the glass, topped with crème fraîche steeped in lavender and three dollops of osetra golden caviar. Definitely a once in a lifetime thing to try.

  2. The River Tavern- their ingredients are all locally sourced and prized for their farm-to-table cuisine. I absolutely love everything on the menu but my favorites include the White Wine Mussels, the Pan Seared Scallops and make sure you order the Date Pudding ahead of time... it's insane.

  3. Rustica Ristorante- the craft cocktails are amazing (and strong), and the food is to die for. I highly recommend the Artichoke Heart appetizer and the Pan Seared Half Chicken for your entrée. I recommend going on Wine Wednesday for 30% off of all wine bottles!

Top Takeout Picks

  1. Thai Riverside- this is definitely one of the best thai food places in the area, perfect for takeout. Their lunch menu is typically a better deal so I'd recommend going then. They do contactless free delivery too!

  2. Hot French Chicks- this is definitely a go-to in my family for takeout. The menu features unique french cuisine that is just mouthwatering. I recommend the Crispy Spiced Chicken Bahn Mi and the HFC Spicy Fried French Creole Chix.

  3. Otto's Pizza- a sister restaurant to The River Tavern, Otto features fresh made brick oven pizza and salads, a little more upscale than Moravelas, and slightly more expensive. I recommend the Caesar Salad and the Classic Margherita Pizza.

Delicious Dessert (obviously needed a section just for this)

  1. Honeycone- a recent 2020 addition to Chester, this creamery offers exotic ice cream flavors and drinks, already recognized on CT news channels. I recommend the Honey Lavender ice cream, the Earl Grey, and the Dairy Free Coconut ice cream. Be sure to wear your warm clothes because there is always a line out the door (even in the winter)!

*Pictured: Grano Arso, Simon's Marketplace, and Honeycone Craft Ice Cream

Things to do

It happened to Jane Filming- a 1959 romantic comedy filmed entirely in the small town of Chester.

Chester Historical Society- Discover Chester's rich history with a tour through the Historical Society Museum.

Take a walk behind the Herbery- Explore one of the many interesting aspects of Chester including a walk through the herbery to the gazebo.

Chester Ferry and Gillette's Castle- A quick 5 minute ride across the Chester Ferry leads you straight to the famous Gillette's Castle. Here, you can take a tour or hike around the property along the Connecticut River.

Visit the Chester Library- The Chester Library has been around for many years serving as a place for Chester families to shop for books and read in the isles.

Skate Jennings Pond- In the winter, numerous Chester residents walk down to Jennings Pond on spring street in Chester to play hockey with whomever shows up that day. Just make sure the ice is solid before you skate, it's not always monitored for safety!

*Pictured: Gillette's Castle, Jennings Pond

Places to Stay

Since Chester is such a small town, lodging arrangements are not plentiful in the downtown area. There are, however, some beautifully unique places on Airbnb to stay and a few great hotels close by.

Popular Airbnb Locations:

  1. Guest Room in the Artist's Garden

  2. Riverfront Cottage

  3. Chester Village 'Pied-à-terre' above art gallery

  4. Waterfall Escape

  5. Chester Cottage

Hotels Nearby:

  1. The Copper Beach Inn, 10 mins from Chester

  2. Riverwind Inn Bed and Breakfast, 5 mins from Chester

  3. The Griswold Inn, 15 mins from Chester

  4. Boardman House, 20 mins from Chester

  5. The Ivoryton Inn, 15 mins from Chester

Located on the hillside of the Connecticut River, Chester is home to a number of lakes, marinas, waterfalls, and acres of state forest perfect for hiking. In Chester, we like to celebrate community, the outdoors, art, cuisine and music. We cherish our small town way of life and welcome anyone who chooses to experience it. Just two hours from both New York City and Boston, you can easily visit by car, train, or air! I encourage you to visit our small town and see what it has to offer! I guarantee you'll want to stay longer.

Check out our merchandise to accompany you on your next roadtrip! This phone case is perfect for your next small town vacation.


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