After an early ferry ride or drive, fuel up at Olive Oyl’s (6 Main St.) all-day cafe in a converted gas station — complete with vintage petrol signs and pumps. Try one of co-owner Jennifer’s blueberry muffins with an Illy espresso.
Stroll down the rest of Essex Village’s Main Street toward the Connecticut River, which made this town an important port and shipbuilding center in Colonial America. It’s impossible not to do a little real estate fantasizing as you pass homes with placards dating as far back as the 1700s. Kids (and adults) will love Toys Ahoy! (43 Main St.) toy shop and Essex Duck (51 Main St.), a store that sells rubber ducks — and only rubber ducks — in all colors, sizes, and themes. Stop by Weekend Kitchen (16 Main St.) dream day for French pot holders and fancy condiments, and Cortland Park (23B Main St.) for luxe cashmere sweaters and cotton shirting.
No day in Essex is complete without a stop at The Griswold Inn (36 Main St.). “The Gris,” as it’s affectionately called, is one of the oldest continuously operated inns in the country, having first opened its doors in January 1776. Today, you can get a standout clam chowder and potato-crusted fish and chips in the inn’s dining rooms.
Book the two-and-ahalf- hour journey on the Essex Steam Train & Riverboat (1 Railroad Ave.). The experience begins with a ride up the Connecticut River for lit-up foliage and a view of Gillette Castle. Returning to Essex, guests board a steam-powered train and ride through nearby towns of Deep River and Chester.
Grab a pre-dinner cocktail — and maybe some plump oysters from Niantic Bay 20 minutes east — and watch the yachts go by at Carlson’s Landing (63 Main St.) overlooking the Connecticut River at the Essex Boat Works marina.
Your table tonight is at The Essex (30 Main St., Centerbrook), helmed by chef-owner Colt Taylor, who was previously the executive chef at One if by Land, Two if by Sea in Manhattan. Taylor’s ever-changing menu beautifully showcases Connecticut River Valley produce and New England seafood.
The Griswold Inn offers 34 antique-filled rooms, some including fireplaces. For something a little more modern (as in, only dating back to 1889), the elegant The Copper Beech Inn (46 Main St., Ivoryton) is great for couples.