Connecticut River Towns: Chester CT to Haddam CT – Charming Towns Just Six Miles Apart

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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 1968, the Victorian confection that is the Goodspeed Opera House has sent 19 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. 

Things To Do Along The Connecticut River

BEGIN in the tiny 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 here, 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.

Interior Harvest Moon - Chester CT
Harvest Moon Chester CT

SHOP: Harvest Moon 

Formerly Elle Design, Harvest Moon, owned by the brightly named Erica Sunshine and Adam Pipkin, excels in modern design, using organic and salvaged materials. Furniture and home accessories are both unique and refreshingly moderately priced. You’ll find things here you won’t find anywhere else, like “guilt-free vegan antlers.”

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.

C and G shop in Chester CT
C & G, Chester CT


Short for Cummings & Good, this unique clothing store focuses on neutral, subdued colors and interesting, unusual textures.  For both men and women, accessories and clothes are comfortable and, just as important, reasonably priced.

The French Hen, Chester CT
The French Hen, Chester CT

SHOP: The French Hen 

You’ll find eclectic home decor, jewelry, clothes, and gifts in this cute, artsy, feel good, independently owned shop.

Chester-Hadlyme Ferry

DRIVE: on Route 154 N. to Ferry Road (about ½ mile) to the Chester-Hadlyme Ferry (April 1- Nov. 30, $5 per vehicle).

On the National Historic Register, this CT River crossing was established in 1769 (it’s the second oldest operating ferry in the country. The 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 CastleEast Haddam 

This eccentric, jaggedly organic medieval structure was conceived in 1919 by William Gillette – who made his fortune portraying Sherlock Holmes on stage. Though the majestic 184-acre grounds are open year round, you can tour the home only from Memorial Day weekend to Labor Day weekend ($6 adult, $2 child). It’s worth it to see the quirky interior, carvings and hardware.

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 (the last Eagle’s nest was documented in 1948 in Hamburg Cove) did the noble birds began to return.  These days, Eagle Cruises are the most popular attraction during the winter months, though you’re likely to see these symbols of America throughout the year.

DO: Cruise on Riverquest East Haddam

Under the Swing Bridge; Captain Mark Yuknat and his wife Mindy, provide a one and a half hour annotated ride on their 54’, 50-person vessel, Riverquest, with its mission to educate groups about the history, ecology and use of Connecticut’s mightiest river.

Much of the land fronting the Connecticut River belongs to the Nature Conservancy, Lyme Land Trust or other wealthy landholders, and as such looks the way it must have looked when old Clippers got caught up on the ubiquitous sandbars that make the entrance to the Connecticut River so treacherous.

The rare Virginia Rail bird still breeds here, and Ospreys find comfy accommodations in mid-river day markers. Cruise times and dates vary throughout seasons, $20pp for 90-minute day cruise. 

SEE: A Musical at Goodspeed Opera House

Built in 1876, marked for demolition in 1958, and saved at the 11th hour to be reborn in 1963, this beaut of a building right on the river (with dock space, even) is “dedicated to the preservation and advancement of musical theater.” On the docket for 2018: The Will Roger’s Follies, Oliver!, and Woody Allen’s Bullet’s Over Broadway.

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

Where To Eat 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 set off by bright red stools and vibrant local art set the stage for tantalizing from-the-ground- fresh cuisine.

Grano, Chester CT

EAT: Grano Arso Chester

To say that the advanced buzz about this just opened (Nov. 2017)”locally inspired, seasonal, all natural” Italian restaurant, helmed by chef/owner Joel Gargano, has been extremely positive is an understatement. Locals are raving about this new kid on the block. 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

 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.  Along with coffee and Morning Glory muffins, you can pick up some Meyers cleaning products, a Sigmund Freud Action Figure, pour-your-own olive-oil, and an ice-cream cone, among a bounty of other knickknacks.

EAT: Blue Oar. Haddam

From Mother’s Day to Labor Day, this Caribbean-yellow spot, ample decks filled with colorful tables and chairs, sparking lights, far from any downtown, overlooking the Connecticut River, is full to bursting. Great food and perfect setting for a night of bliss, it’s where river rats go when they grow up.  BYOB, Cash only.

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; where the outside patio generally throngs with serious lager drinkers till 2am.

Where To Stay Along The Connecticut River

Nehemiah Brainerd House, Haddam CT

STAY: Nehemiah Brainerd House. Haddam, CT.  It’s just six miles from Chester and three from the Goodspeed Opera House, run by the kind of people who say, “Our guests are either really nice, or really, really nice.”

Katharine Brush, Nehemiah Brainerd House, Haddam CT

Once owned by New York writer and glamour-girl, Katherine Brush, this stately 4 room, one-cottage B&B on a bluff overlooking the Connecticut River had “gone to seed” by 2002 when Maryan and Jeff Muthersbaugh discovered it.  They worked on the home – part of it built in the 1700’s and two wings added in the 1920’s – every weekend for nearly seven years, then began taking guests in 2009.

Since then, the Brainerd House has been featured on the HGTV show “If Walls Could Talk” and in 2011, Yankee Magazine bestowed its “Best Hilltop Cottage” in New England on the B&B’s separate honeymoon cottage.

Tea Set at Nehemiah Brainerd House, Haddam CT

Ask Maryan or Jeff to crank up the 1904 Columbia Records Graphaphone in the dining room (it still works; just missing a Fox Terrier) while you feast on a candlelit breakfast that includes Maryan’s sinful signature baked apple.

STAY: Two inns are just steps from the Goodspeed Opera House in East Haddam.  Stay in opulent luxury at the Boardman House or welcoming comfort at the sweet Bishops Gate Inn, where “an expansive start-your-day breakfast” emerges from the “4-star kitchen.”

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 – and another Maven Favorite with its own write-up covering the hidden gem town of Killingworth CT.

3 thoughts on “Connecticut River Towns: Chester CT to Haddam CT – Charming Towns Just Six Miles Apart”

  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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