Some of my favorite foliage views aren’t from a mountaintop. They’re from the car on River Road when the leaves have started falling and the river suddenly peeks through. They’re from a dock in Essex, or the deck behind the Gillette Castle visitor center, or Harvey’s Beach at low tide when you can walk out onto the sandbars.
This is the fall drive I would take if I had a whole day, good company, and absolutely no desire to hurry. It begins and ends at Grace & Haven in Essex Village and winds through Deep River, Chester, East Haddam, Old Saybrook, and back home. You can do a shorter river-only version or take the long way to the Sound.
Route at a glance: Essex Village → River Road and Deep River → Chester → East Haddam and Gillette Castle → Old Saybrook Point and Fenwick → Harvey’s Beach → Essex. Important for fall 2026: The Chester–Hadlyme Ferry is listed as closed until further notice as of September 24. Use the Route 82 East Haddam Swing Bridge to cross the river and check CTroads before leaving. If ferry service resumes, you can restore that short crossing to the route.
1. Begin in Essex Village
Start with coffee at Olive Oyl’s and a walk down Main Street to the river. If you have time, sit by Steamboat Dock and watch the ducks. Then head up past North Main and out toward River Road. For a full morning in town before the drive, use my fall guide to Essex.
2. Follow River Road toward Deep River and Chester
River Road is beautiful any time of year, but fall changes it. As the leaves turn and thin out, you get more glimpses of the Connecticut River. This is a slow, winding road; pull over only where it is legal and safe, and let the drive itself be the point. Continue through Deep River and into Chester.
Chester has a different energy from Essex and is worth a stop, even if it isn’t your entire day. If you’re driving on a Sunday, look up the Chester Sunday Market. My personal order is a banana latte at Three Fates, maybe a kielbasa breakfast sandwich from The Villager, and a little time wandering town. Little House Brewing is a great later stop; on a warm afternoon, make it Honeycone ice cream. If you’re staying for dinner, I love The Village Bistro.
3. Cross to East Haddam for Gillette Castle
My usual dream version of this drive includes the tiny Chester–Hadlyme Ferry. It is currently closed until further notice, so please do not route yourself to the ferry landing expecting to cross. Continue to the East Haddam Swing Bridge on Route 82, cross there, and drive up to Gillette Castle State Park in East Haddam. Verify bridge travel conditions before departure as well.
The views from the grounds are why I come back. Walk to the patio behind the castle and the deck behind the visitor center. The grounds are wonderful on their own; state park information has current details for tours and access. One family detail I love: the restoration of William Gillette’s train on display at the visitor center was spearheaded by my dad and others locally.
If you have tickets and time, catch a show at Goodspeed Musicals and make this the day’s final destination instead of trying to fit in the whole loop.
4. Follow the river south to Old Saybrook
From East Haddam, cross the swing bridge and take the route south toward Old Saybrook. This is the point where the day can become an all-day adventure. Head down Main Street to Saybrook Point, drive along the causeway and through Fenwick, then follow the shoreline. It’s the kind of slow drive I daydream about when I’m somewhere else.
If the tide and public access conditions allow it, finish with a walk at Harvey’s Beach. Low tide is my happy place. Check the town’s current beach access and parking rules, particularly if you’re visiting from outside Old Saybrook.
5. Come back to Essex for dinner
Return to Essex for a drink at Noah’s or dinner and Tap Room music at the Gris. If you’ve spent most of the day outdoors, chowder tastes even better. There is no prize for fitting in every stop. Skip half of this itinerary if that gives you more time to actually enjoy the other half.
Want more stops near this route? I collected my favorite fall outings near Essex, including Chapman Falls, farms, Hammonasset, and river excursions.
Practical notes before you drive
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Ferry: Check CTroads alerts. The Chester–Hadlyme crossing was closed until further notice when this draft was prepared September 24, 2026. The bridge route works without it.
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Timing: Allow most of a day if you want to stop in both Chester and Old Saybrook. The route is flexible; traffic, bridge conditions, meals, and walks determine the real duration.
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Foliage: Color shifts by year and by location. Don’t promise yourself a single “perfect peak” weekend; the river, historic villages, and shoreline are lovely at different stages.
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Access: Check official park, beach, restaurant, ferry, and bridge notices before leaving.
Frequently asked questions
Where can I see fall foliage near Essex, CT?
My favorite nearby views are River Road between Essex and Deep River, the grounds at Gillette Castle in East Haddam, the riverfront in Essex, and walks around Cross Lots. The drive toward Chester adds river scenery, while Old Saybrook gives you an entirely different coastal finish.
Can I do the loop without the Chester–Hadlyme Ferry?
Yes. Cross on Route 82 at the East Haddam Swing Bridge to visit Gillette Castle, then use the bridge again when you continue south. Check live traffic alerts before setting out.
Is this drive good with kids?
Yes, if you choose a few stops rather than asking them to enjoy hours in the car. Ducks in Essex, a short walk at Gillette Castle, and a beach stop work well. For a more kid-centered day, see my October family guide.
Starting point: Grace & Haven, 23 Main Street, Essex, CT. Stop in before or after the drive and tell me which stretch you loved most.
Amy Ihrke is the founder of Grace & Haven, a women’s, baby and kids, and gift boutique on Main Street in Essex, Connecticut. She grew up in Essex, moved away, and came back to experience the town through her children’s eyes. These guides share the places she actually goes, the traditions her family loves, and the local businesses she’s always telling friends and customers about. Find her at Grace & Haven, 23 Main Street.
