Exploring the Connecticut River Valley

Just a short drive south from bustling Hartford and north of elegant New York City adjacent Fairfield County lies the sleepy Middlesex County. When I am planning to spend time in Connecticut, with girlfriends or my family, we often head to this area to enjoy its beautiful forests, uncluttered shoreline, and intriguing history. Here are some of my recommendations for spending a day in the Connecticut River Valley and one of my favorite towns, Essex.

24 Hours Around Essex Connecticut
Gillette Castle overlooks the Connecticut River.

Things to Do in Essex, Connecticut

24 Hours in Essex Connecticut
A decorated window box on Essex’s docks.

Essex is one of my favorite New England towns and was dubbed one of “the 100 best small towns in America”.

Take a Stroll along Main Street

It has the quintessential New England downtown- perfect for walking, shopping, and people-watching along the pedestrian-friendly Main Street lined with early Colonial and Federal-era houses.

Enjoy a Leisurely Drink at the Griswold Inn

The inn, started by three brothers in the late 1700s, is the oldest continually running tavern in the US.

Enjoy the Banks of the Connecticut River

Essex is surrounded on three sides by the Connecticut River. You can catch a big boat ride on the Connecticut River Boat or…

Take a Ride on the Essex Steam Train

My great-grandfather was a train engineer, so my family loves to explore really cool trains. We love to ride in these cool old vintage coaches through the untouched nature along the Connecticut River taking in such sites as Gillette Castle, the East Haddam Swing Bridge, and the Goodspeed Opera House. Speaking of Gillette Castle… Head to

Things to Do in East Haddam, Connecticut

Things to do in East Haddam, Ct
This view of the Connecticut River is a welcome reward after the hike up to Gillette Castle.

Explore Gillette Castle

After your train ride, drive down to the Chester-Hadlyme Ferry to travel over to the very kooky Gillette Castle. I know what you are thinking. The United States doesn’t have castles. We do when movie stars build them. Think of it as a cross between California’s Winchester Mystery House and a European castle. The castle was built with great imagination by the Sherlock Holmes stage actor William Gillette. Sitting high on a cliff over the Connecticut River, getting to the castle provides a lovely hike. In season, you can tour the house and find the surprises in it. Even when the house isn’t open, it is worth visiting.

Visit Gillette Castle, Connecticut.
Hidden in the intricate stonework of Gillette Castle, you can find animals. Just some of the fun in store at this state park.

Get Impressed by Old Lyme

Florence Griswold Museum

Exploring the Connecticut River Valley
The panels in the dining room of Florence Griswold’s boarding house were painted by early American Impressionists when they stayed.

I am such a fan of impressionism! This museum is a gem. Started in the early 1900s in Florence Griswold’s boarding house, the Lyme Art Colony is the birthplace of American Impressionism. The museum’s simple white walls are the perfect place to showcase its impressive collection, although the panels in the boarding houses’ dining room are incredible too. You will understand the inspiration for these works further with a stroll through the gardens. The perfect way to end your day is with a meal on the back porch on the banks of the Connecticut River.

Exploring the Connecticut River Valley. www.thedailyadventuresofme.com
The lunch view from the Florence Griswold Museum restaurant

Lastly, Head Down to the Water’s Edge in Westbrook

Read on to explore the best things to do in Central Connecticut, including steam trains, hiking a castle. #essexct #Connecticut #NewEngland #TBIN
Even in the winter, a walk on the beach in Westbrook, Connecticut, to see the sunset is sublime.

The grounds of the Water’s Edge Hotel, set on the Long Island Sound, will provide the perfect end to your day of nature, New England charm, and history. You can see more about my time here in How a Breakation Can Improve Your Winter Mood.

Enjoy your time in the Connecticut River Valley. Please let me know about it in the comments. Also, let me know if you have been and have other suggestions.

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8 thoughts on “Exploring the Connecticut River Valley”

  1. Hi! Is it possible to see your suggestions in Essex and East Haddam in a day trip from New York City? Would you make the same recommendations if traveling in December? MANY thanks!

    • The town of Essex is beautifully decorated for Christmas. I have spent whole days wandering there and shopping in December. The castle and boats are likely closed.

  2. My family is new to the area, we’re so excited to be here! Based on this list it looks like there are so many fun things to do! I think our kids will absolutely love the Essex Steam Train and exploring Gillette Castle! Thanks for the great list of things to do!


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