Upcoming events.


November First Friday
Nov
1

November First Friday

For an evening of good food, good friends and good times, there’s no better place than Chester. First Fridays are maybe a lot bit better due to live music all evening and the shops open late.

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Chester Sunday Market
Oct
13

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

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Chester Sunday Market
Oct
6

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

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First Friday Arts Stroll
Oct
4

First Friday Arts Stroll

There’s a lot going on this crisp & clear

First Friday, Oct 4th, 5-8 pm

Leif Nilsson Spring Street Studio and Gallery

Enjoy some of the oldest and newest paintings of Leifs home and travels for a happy hour or two in the gallery with live music by Arrowhead from 5-8pm.

One Spring Street  (860) 526-2077  www.nilssonstudio.com

Chester Gallery

860-449-3617chestergalleryct@gmail.com

Celebrate the change in the season for  'Local Color in Autumn' during this First Friday Stroll.  The exhibition features works by Sean Kratzert, Judy Perry, Nancy Pinney, with gallery artists - pictured left to right - Sol LeWitt, Richard Ziemann, and Elizabeth Gourlay.

Join us from 5-8 for great art and live music!

Little House Brewing

Little House will be having a gallery opening on First Friday for Skip Marsh. We're also kicking off spooky season by decorating for "Little House of Horrors" and pouring our fall beer specials, Nikki Sixx (Pumpkin Pie Porter) and Apple Cider Jonas (Scotch Ale with Apple Cider Donuts, Caramel, and Coffee).

Montgomery & Taggert Bookshop

Find your happily ever after in Chester at Connecticut's 1st romance-themed bookstore! Join us for extended hours until 8pm on Fri. 10/4 to shop books and gifts and taste a sample of ImmuneSchein Ginger Elixers. Get cocktail/mocktail recipe suggestions and reading recommendations for spicy book pairings to enjoy with your elixir!

Pattaconk is featuring all new fall cocktails with an Autumn Margarita, Titos Appletini, Hoodie Season with hot apple cider & more! Including all new delicious dinner specials! Also don't forget our Sunday Bloody Mary Bar & Brunch plus Trivia Thursdays!

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Chester Sunday Market
Sep
22

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

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Come Home to Chester
Sep
20

Come Home to Chester

The Pattaconk will be offering a selection of new and exciting Fall cocktails


NOW OPEN - Check Them Out!!

Montgomery & Taggert Bookshop

26 Water Street -  www.montgomeryandtaggert.com

Find your happily ever after in Chester at Connecticut's 1st romance-themed bookstore! Join us for extended hours until 8pm on Fri. 9/20 to shop books and gifts and taste a sample of ImmuneSchein Ginger Elixers. Save the date for our Grand Opening Celebration on Sat. 9/21 from 10am-6pm for fun giveaways and vendor popups in the garden. 


Leif Nilsson Spring Street Studio & Gallery

Enjoy some of the oldest and newest paintings of Leif’s home and travels for a happy hour or two in the gallery with live music by Paddy Whack from 5-7pm.

One Spring Street  (860) 526-2077  www.nilssonstudio.com

Inner Saybrook Light
oil 6 x 24 inches
Leif Nilsson summer 2024 ©


Chester Gallery

Join us for a closing reception of our exhibition 'Local Color in Summer' when we celebrate the last days of the season for the Come Home to Chester Stroll. The show features works by Deborah Quinn Munson, Judy Perry, Judy Friday with gallery artists Sol LeWitt, Elizabeth Gourlay, and Richard Ziemann.

The Chester Gallery Annex at 45 Main Street invites you to meet Moya Aiken, who will be giving a gallery talk about her art and critically acclaimed memoir 'Shoulder' at 6 pm. Please contact Nancy at chestergalleryct@gmail.com to attend this free event. This pop-up show ends on Sunday, October 13th

Chester Gallery - 76 Main St. Chester - 860-449-3617  chestergalleryct@gmail.com


The Wayfinder Society

We have no idea what we are doing Friday night, however it will be groundbreaking! Drinks will definitely be involved. We will maybe learn how to dance the “Tighten Up” (look it up on YouTube) on the porch. We will absolutely have a bunch of new curiosities, whimsies, and other shockingly cool stuff.

14 Main Street - 860.322.3905 - TheWayfinderSociety.com


See You On Friday


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Chester Sunday Market
Sep
15

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

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Chester Sunday Market
Sep
8

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

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Sep
6

First Friday Stroll

Join Us For A First Friday Night Art Stroll


This Friday, September 6th, 2024 from 5 - 8 PM

With everyone open late, there is a lot going on this month.

Here’s just a sampling…

Arch One Glass 

51 Main St. - 860.575.5033

arch1glass.com

Will be demoing making glass mushrooms. From 5:30 -7:00

Acoustic Music

4 Maple Street - 203.458.8353 acousticmusic.org

Karen Hogg will sing John Hartford songs from 6-7pm om the lawn.

Chester Gallery

76 Main Street - 860.449.3617 - www.chestergalleryct.com

Cool off with Chester Gallery's summer show, Local Color! Featuring new works by Deborah Quinn Munson, Judy Perry and Judy Friday, along with gallery artists Sol LeWitt, Richard Ziemann, and Elizabeth Gourlay. The Annex at 45 Main is continuing with works by Moya Hession Aiken where she will be signing her memoir, Shoulder. Music on the porch with The Gibbons.

Lark

4 Water Street - 860.322.4256

Stop into Lark for your fall wardrobe essentials! Our alluring collection features vibrant violets, brilliant blues, gorgeous greens, radiant reds and much more. Let us help you find what you need for the changing season.

The Wayfinder Society

14 Main Street - 860.322.3905 - www.TheWayfinderSociety.com


Hear: Anything Goes playing outside on the porch.

See: Two particularly cool new curiosities (Antique Japanese Kanban, 75-100 BCE Roman coin)

Taste: Spirits and Libations (and maybe a foreign snack or two)

Leif Nilsson Spring Street Studio & Gallery

One Spring Street  (860) 526-2077  www.nilssonstudio.com

Enjoy some of the oldest and newest paintings of my home and travels in the gallery for a happy hour or two with Live Music on the porch by Paddy Whack while local author Joan Giarratano is signing and reading her book “The Boy in the Mirror”.

Dina Varano Gallery

27 Main Street - 860.526.8866 - dinavarano.com/

Join us for Chester’s First Friday, September 6th from 5-8pm. Featuring a coveted collection  of oxidized sterling silver, 14 karat gold, Tahitian pearls and gemstone necklaces. Come by and try one or all of these pieces on! All handmade in Dina’s studio in Chester. Refreshments will be served. Hope to see you!

See You On Friday!

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Chester Sunday Market
Sep
1

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

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Chester Sunday Market
Aug
25

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
Chester Sunday Market
Aug
18

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
Chester Sunday Market
Aug
11

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
Chester Sunday Market
Aug
4

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

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August First Friday Stroll
Aug
2

August First Friday Stroll

Please join the Merchants of Chester for our June First Friday celebration.

First Fridays are a family-friendly event held in Chester Village from 5-8pm. These lively strolls often feature new art exhibitions, exciting seasonal menus & ice cream flavors, live music, and great shopping.

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Chester Sunday Market
Jul
28

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
Chester Sunday Market
Jul
21

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
Chester Sunday Market
Jul
14

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
Chester Sunday Market
Jul
7

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

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July First Friday Stroll
Jul
5

July First Friday Stroll

Please join the Merchants of Chester for our June First Friday celebration.

First Fridays are a family-friendly event held in Chester Village from 5-8pm. These lively strolls often feature new art exhibitions, exciting seasonal menus & ice cream flavors, live music, and great shopping.

View Event →
Chester Sunday Market
Jun
30

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
Chester Sunday Market
Jun
23

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
Chester Sunday Market
Jun
16

Chester Sunday Market

Held every Sunday through October 11th, 2024 from 10 am - 1 pm on Main Street in Chester Village. Local produce, fish, bakery items, pizza truck, live music, and more! Great for the whole family!

For a list of market vendors, the bands playing each week, and more: https://chestersundaymarket.jimdofree.com/

View Event →
June First Friday Stroll
Jun
7

June First Friday Stroll

Please join the Merchants of Chester for our June First Friday celebration.

First Fridays are a family-friendly event held in Chester Village from 5-8pm. These lively strolls often feature new art exhibitions, exciting seasonal menus & ice cream flavors, live music, and great shopping.

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May Daze First Friday Stroll
May
3

May Daze First Friday Stroll

Please join the Merchants of Chester for our May Daze First Friday celebration.

First Fridays are a family-friendly event held in Chester Village from 5-8pm. These lively strolls often feature new art exhibitions, exciting seasonal menus & ice cream flavors, live music, and great shopping.

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Chester Earth Day
Apr
20

Chester Earth Day

Join us in the heart of Chester, Connecticut, for a vibrant celebration of our planet on Saturday, April 20th, 2024, from 9 AM to 5 PM.

This year, we're excited to present a lineup that will enrich your connection to our planet and its future. Main Street will be closed to vehicles from 12pm-5pm.

Schedule of events: https://www.chesterearthday.com/

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April First Friday Stroll
Apr
5

April First Friday Stroll

Please join the Merchants of Chester for our monthly First Friday celebration.

First Fridays are a family-friendly event held monthly in Chester Village on the first Friday of every month from 5-8pm. These lively strolls often feature new art exhibitions, exiting seasonal menus & ice cream flavors, live music and great shopping.

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First Friday Stroll
Mar
1

First Friday Stroll

Please join the Merchants of Chester for our monthly First Friday celebration.

First Fridays are a family-friendly event held monthly in Chester Village on the first Friday of every month from 5-8pm. These lively strolls often feature new art exhibitions, exiting seasonal menus & ice cream flavors, live music and great shopping.

View Event →