Charming Chester


If you’re looking to describe Chester, handmade is a good place to start. This hamlet is well known for its bevy of artists and artisans, and a clutch of shops that are ready to satisfy even the pickiest of people. You’ll find handwoven baskets and scarves, original jewelry and gems, crafted-right-in-the-shop leather bags, and all manner of ornament. Spend a day in Chester, and you will check everyone off your list. Now that it’s my little town, too, I see (and eat!) the best of it every day. Plan on staying for lunch or dinner, we’ve got the best restaurants per capita, too. Enjoy a craft beer at our very own Little House Brewery or reviving tonic (or espresso or chai) at Tonic.

The E List Shop!

The historic columned stone building at the crossroads of Main and North Main now houses everything E List. Upstairs we’re busy writing, editing, and photographing the articles for our weekly excruciatingly opinionated newsletter about the best of the Shoreline. Downstairs in the shop, you’ll find an equally thoughtful mix of modern and stylish clothing and accessories for women from designer brands unavailable elsewhere. Shop The E List online here.

Velvet Jacket



The Herbery: 26 Water Street
Maureen has long been known for her handmade wreaths, and while it’s too late to special order, she’s always got some strewn about the shop and garden. Not to miss is her astonishing array of French ribbons, canisters of organic spices by the ounce, lovely topiaries (a great gift in lieu of flowers in my book), and the perfect battery-powered candles for your holiday windows (that could pass for real).


French Hen: 14 Main Street
A well-known destination for giftable goodies (many with a French accent), Laurie has done it up this year with an astonishing selection of ornaments. Blown glass hot air balloons, lovely swans, delicate angels, many of which are handmade. Puzzles, cheap and cheerful jewels, candles, and plenty of host/ess with the mostest gifts here.


Dina Varano: 27 Main Street
A stalwart in Chester, folks have been coveting collections of Dina’s bench-made jewelry for over 25 years. Lately, she’s been adding 14k gold to her array of sterling silver jewelry, and I flipped for these oversize hoops and pearl pendants. You’ll also find that perfect cashmere scarf by Chan Luu, an assortment of well-priced beaded bags (this one is $92), and lovelies for the table, like these handmade candlesticks ($170).


Blackkat Leather: 36 Main Street
Drew Archer, the designer behind this leather atelier, creates all their stunning bags right here in the shop. Known for classic design and minimal hardware, the bags are one of those eternal investments that get better with age. Bags, briefcases, overnighters, and more for men and women. Briefcase $25, Overnighter $845, Zip top tote $295, Belts $50 to 60


Kismet: 11 Main Street
Gillian Davis hand beads her jewelry collection and augments her inventory with a variety of fun, well-priced (and often local) giftables. These rainbow multi-strand glass beaded necklaces ($275) and Druzi with tourmaline quartz matching set caught my eye.


The Perfect Pear: 51 Main Street
This foodie destination has everything a cook will ever need plus a variety of local products, including these standout knives with Damascus steel blades and handles made right here in Old Saybrook.


Tonic: 1 Main Street
The newest addition to our town is a wonderfully welcome one! Known nationally for their fantastic line of local teas, they’ve expanded here to offer housemade tonics to cure what ails you, a curated selection of CBD products, and their entire range of gorgeous and giftable teas. Flagging? Stop in for an espresso, cappuccino or chai, too.


Lark: 4 Water Street
It’s easy to get lost in Lark’s sprawling (especially for Chester) space. We easily spied these darling hand-felted figures ($21) embodying the likeness of such icons as Ruth Bader Ginsburg, Gandhi, John Lennon, and many more. These collectible beauties are made by a woman-led, women-run Fair-Trade cooperative in the mountains of Kyrgyzstan. Also found: some fun, easy cookbooks that are perfect for gifting!



Strut Your Mutt: 29 Main Street
For the dog-parent in your life, consider gifting a trip to the Pet Spa at Strut Your Mutt. Either DIY/Self Serve for $20 or Full Service for $35. DIYers have access to aprons, shampoo/conditioner, towels, and a professional hairdryer. Grab one of these spiffy collars to complete pet pampering. $25.99 to $35.99


Swoon/Lori Warner Gallery: 21 Main Street
Among the careful collections of perfume, foodie accouterments and objets d’art in Lori Warner’s downstairs gift shop, partner to her upstairs fine art and jewelry gallery, you’ll find the sweetest gifts for kids. We went wild for these hand-embroidered, linen, goose-feather and down-stuffed pillows (removable; for delicate wash). $82.  Also, these handmade walnut and maple penguins are hard to resist. $12 each


Antiques at The Mill: 5 West Main Street
You can browse with ease through room after tiny room at this local antique shop as owner Karen Hart has done a thoughtful job merchandising and grouping all manner of treasures by color and function. We loved the vintage bakeware and a table of white serving pieces.



Leif Nilsson Spring Street Studio and Gallery – 1 Spring Street

Chester Gallery & Framing – 76 Main Street

Helene Johnson1 West Main Street 860-767-0445


Where to Eat:

Grab Lunch at: 

Simon’s: 17 Main Street Don’t leave town without a buttery salty baguette, plus casual breakfast and lunch and to-go.

Wheatmarket: 4 Water Street Our go-to for soups and sandwiches and classic candies.

Villager: 13 Main Street Creative and fresh breakfasts and lunch.

Thai Riverside: 4 Water Street Their Thai Sampler will cover all your cravings, plus we’re huge fans of the chicken fried rice and fresh rolls!

River Tavern: The spot that started the farm-to-table movement in Connecticut. Delish as ever for lunch or dinner.

Pattaconk: 33 Main Street Can’t resist the double hot dogs and popcorn.

Grab dinner at:

Grano Arso: Locally sourced, House-milled grains and pasta but me, I’m ALL about the roast chicken. Creative cocktails, too.

River Tavern: See above

Thai Riverside: See above

Otto Pizza: Open for lunch on weekends, dinner every night. Our pick for best pizza from farm-fresh and local ingredients.


Where to park in Chester:

Take exit 6 off Route 9 and head towards downtown (Right if RT9N, Left if RT9S). If you see a spot on the street in town, go for it!

There is a lot on Water Street just before RJ Vickers’ Herbery on the right. Head straight through stop sign at corner of Main and Water Streets, 1/10 of a mile from The E List Shop.

There’s another lot just past OTTO on the left. It’s just inside the entrance to the Laurel Hill Cemetery.

The best spot to park is at the Maple Street Lot, take a right off Main Street to Maple Street and it’s on the left. Look for the Parking sign. It’s a large lot and there are usually plenty of spots. Short little stroll down the path to town.

And, of course, if you’re shopping at The E List, you’re welcome to park in our private lot!

Here’s a map:

Chester CT parking map