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.

Things to Do in Essex, Connecticut

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

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.

Get Impressed by Old Lyme

Florence Griswold Museum

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.

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

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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