A Day in Essex With Rivers, Rails, and Revolutionary Tales

Start your day with a step back in time. The Essex Steam Train & Riverboat is part history, part adventure, and 100% unforgettable. Feel the rumble of a vintage locomotive beneath your feet as you chug through the Connecticut River Valley, then climb aboard the riverboat for panoramic views and breezy vibes. 

Next, wander the walkable downtown, where local boutiques like Riverlane offer everything from chic fashion to artisanal gifts. Riverlane even has an in-store concierge styling service (yes, with wine!) if you're looking to level up your look.

Three floors of fascinating exhibits and river views? Yes, please. The Connecticut River Museum tells 12,000 years of river stories — from Indigenous history to maritime innovation with the invention of the submarine (yes, it happened here!). Afterward, stroll the docks, take in the riverfront views, or hop on a seasonal sunset cruise.

In nearby Ivoryton, catch a show at the historic Ivoryton Playhouse, where stage legends like Katharine Hepburn and Marlon Brando once performed. Whether you're into musicals or modern dramas, this cozy theatre delivers big talent in a small-town setting. Bonus: the theater still honors its summer stock roots with high-energy productions all season long.

Wrap up your Essex escape at the legendary Griswold Inn, operating since 1776 and still one of the coziest spots around. Enjoy dinner at the wine bar, sip one of 40+ wines by the glass, and then stick around — not just for your overnight stay, but for the Sea Shanties on Monday Nights, a beloved local tradition that turns the tap room into a joyful, foot-stomping sing-along. Trust us, you'll leave humming.

Essex is photogenic at every turn. Whether it's the river at golden hour or a vintage railcar rolling by, you'll want to remember every moment.