Skip to content
Women wearing outfits from Grace & Haven in Essex, CT networking over coffee at one of our events
Director at Hope School
Jenny O'leary
Christine Hanford
7 min read
20 Fall Things to Do Near Essex, Connecticut

Essex is a wonderful place to start a fall day, even when the plan takes you somewhere else. These are 20 outings around the Connecticut River Valley and shoreline I actually love, from Chester coffee and river views to cider mills, apple picking, waterfalls, and low-tide beach walks.

6 min read
A Connecticut Fall Foliage Drive: Essex, Chester, East Haddam & Old Saybrook

My favorite Connecticut fall drive starts in Essex, follows the river through Deep River and Chester, climbs to the views at Gillette Castle, and ends with a beach walk in Old Saybrook. Here’s the route, my favorite stops along the way, and what to know about the Chester–Hadlyme Ferry before you go.

6 min read
Fall With Kids in Essex, CT: Scarecrows, Pumpkins & Halloween 2026

October in Essex with kids means scarecrow walks, pumpkin hunts, waterfront ducks, and plenty of reasons to stop for a treat. From FestiFall and the Ivoryton Pumpkin Festival to our family’s favorite everyday stops, here’s how I’d spend a fall afternoon with the kids—and where we go when it rains.