11 Artsy Things to do In Chester CT And Other Adorable Towns On the CT River

WHY GO: Performing, fine and culinary artists, as well as clothing and building designers, have been drawn to the mesmerizing Connecticut River for centuries, and after indulging in this Getaway – to Chester, Haddam and East Haddam –  you’ll see why.

Some of the best artists and chefs in the region create in local kitchens and studios, and since it reopened in 1963, the Victorian confection that is the Goodspeed Opera House has sent 21 productions to Broadway. See a musical, shop in one-of-a-kind (inexpensive) designer boutiques, and end the day with an exquisite meal on this show-stopping Connecticut Getaway.

To expand your getaway, check out this post about Essex CT.

Curious about other dreamy escapes in CT? Check out the Best Romantic Getaways in Connecticut. 

Things To Do in Chester CT, Haddam, and East Haddam

BEGIN:  Artist Colony of Chester CT

Contemporary artist Sol LeWitt, whose work can be found in most world-class modern art museums (and who died in 2007) made his home in Chester CT, and many others have followed. It’s the perfect place to pick up handcrafted jewelry, art, clothing, and crafts directly from the artist for a lot less than you’d pay in New York.

Lark shop in Chester CT
Lark, Chester CT

SHOP: Lark

Lark’s tag line, “A Spirited Adventure,” remarks on the ’round the world aspect of this gift/jewelry/clothing/home goods shop that has expanded to nearly a block long. It’s lots of fun just to browse. Check out other little shops and galleries in town – you’re bound to discover something that calls to you.

BEER: Little House Brewing Co.

The Little House Brewing Co. in downtown Chester is a welcome addition to this CT River town, and another reason that craft beer fans are visiting Chester in droves. Great brews, excellent cider, and friendly service in an adorably historic “little house,” Little House Brewing has the complete package.

HIKE/SWIM: Cockaponset State Forest, Chester, Deep River + 7 Other Towns

Check out the 16,700-acre Cockaponset State Forest if you need a leg stretcher or want to cool off. The second largest State Forest in CT, Cockaponset features 9.3 miles of Blue Blazed trails, and and the Pattaconk Reservoir for swimming.

Chester-Hadlyme Ferry

DRIVE: on Route 154 N. to Ferry Road (about ½ mile) to the Chester-Hadlyme Ferry (April 1- Nov. 30, $6 per vehicle).

On the National Historic Register, the Chester-Hadlyme Ferry  was established in 1769 (it’s the second oldest operating ferry in the country. (The oldest, in Glastonberry, is just upriver) and truly takes you back in time. The short, several minute trip will bring you to Gillette Castle, the rough-hewn granite home of eccentric Sherlock Holmes actor, William Gillette.

Gillette Castle

VISIT: Gillette Castle State Park, East Haddam

This eccentric, jaggedly organic medieval structure, Gillette Castle, was conceived in 1919 by William Gillette – who made his fortune portraying Sherlock Holmes on stage.

Though the majestic 184-acre Gillette Castle State Park is open year round daily 8am to sunset, you can tour the home only from Memorial Day weekend to Labor Day weekend. It’s worth it to see the quirky interior, carvings and hardware. Go to website to book a tour. 

DRIVE: Route 84

Either cross back on the ferry, or drive 4 ½ miles to East Haddam on River Rd. N and take a left onto Route 84. This brings you to the Goodspeed Opera House and historic Steel Truss Swing Bridge.

WATCH FOR: American Bald Eagles

By the mid 1900’s, industrialization had taken its toll on most water bodies in the United States.  Lakes were aflame with combustible chemicals and sewage, toilets flushed directly into rivers and the Connecticut River Valley was loosing one of its most recognizable inhabitants – the Bald Eagle.

DDT made Eagle eggshells weak, and breeding diminished to near extinction.  Only when the water was cleaned up, and after a 50-year absence did the noble birds began to return. (The last Eagle’s nest had been documented in 1948 in Hamburg Cove).

These days, the RiverQuest Eagle Cruises are the most popular attraction during the winter months. However, you’re likely to see these symbols of America throughout the year.

SEE: A Musical at Goodspeed Opera House

The Goodspeed, built in 1876, was marked for demolition in 1958. Saved at the 11th hour it was reborn in 1963 as this beauty right on the river. (It even has dock space). The Goodspeed is still “dedicated to the preservation and advancement of musical theater,” with a fantastic line up every year.

Whitewashed Victorian building on banks of Connecticut River - Broadway Show House - East Haddam CT

Best Restaurants Along The Connecticut River

Dining room of modern farm to table restaurant - white linen tablecloth - open kitchen. - River Tavern - Chester CT

EAT: River Tavern, Chester

Polished wood floors in a room fit for Yoga class, a teak and zinc bar brightened by red stools, and vibrant local art set the stage for tantalizing from-the-ground- fresh cuisine at The River Tavern.

Grano, Chester CT

EAT: Grano Arso Chester

To say that the buzz about this “locally inspired, seasonal, all natural” Italian restaurant, helmed by chef/owner Joel Gargano, has been extremely positive is an understatement. Locals rave about Grano Arso.  Chef Gargano is particularly proud of using house-milled flour for his scratch as it gets Whole Grain Pasta.

EAT LUNCH: Simon’s Market, Chester on the Connecticut River

The heartbeat of Chester is Simon’s Market, a family owned breakfast/sandwich/gift shop that has become the de facto meeting place for locals.  “A lot of great ideas that have been implemented in town are dreamed up here,” locals admit.

Pick up some Meyers cleaning products along with your coffee and Morning Glory muffins. Or, grab a Sigmund Freud Action Figure and an ice-cream cone. There’s certain to be a among a knickknack with your name on it.

Pattaconk Bar and Grill, Chester CT
Pattaconk Bar and Grill, Chester CT

DRINK: Pattaconk, Chester

In the mood for a Dogfish Head, Anchor Steam Beer or Sierra Nevada? Join the jolly crowd at the 1850 Pattaconk. In season, the outside patio throngs with serious lager drinkers till 2am.

Where To Stay Along The Connecticut River

STAY: Boardman House

Stay in opulent luxury just steps from the Goodspeed Opera House, in East Haddam, at the Boardman House.

Sunroom Chatfield Hollow Inn Killingworth CT
Sunroom Chatfield Hollow Inn Killingworth CT

STAY: Chatfield Hollow Inn, Killingworth

Just 15 minutes from the CT River, Chatfield Hollow Inn is a trend-setting in the woods 5-room B&B. It’s a Maven Favorite with its own write-up in the town of Killingworth CT.

Connecticut River Towns Pin


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

3 thoughts on “11 Artsy Things to do In Chester CT And Other Adorable Towns On the CT River”

  1. Thanks for visiting Chester and I’m so glad you enjoyed it. I hope you return soon…possibly for one of our wonderful “First Fridays”. All the shops and galleries stay open until 8pm and offer something festive (and complimentary) to sip while you wander. The next one is December 1 which just so happens to be the night of our tree lighting! Thanks again for the kind words. #shopsmall

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