I love a full day in Essex. I also love using Essex as the starting point for somewhere else: a Sunday morning in Chester, a walk to a waterfall, apple picking with the kids, or a low-tide beach walk because October decided to feel like August.
Here are 20 fall things I actually recommend around the lower Connecticut River Valley and shoreline. They’re a menu, not a challenge to do them all. Pick two or three and leave enough room for the unexpected.
Where to start: Staying in Essex? Begin with my fall day in the village. Want to see several towns in one scenic outing? Take my foliage drive. Traveling with kids during October? Use our family and event guide.
Around Essex and the river
1. Walk Cross Lots Preserve
When I need a proper walk without turning the day into a hike, Cross Lots is my answer. It’s beautiful year-round and especially lovely when the leaves turn. Check the land trust’s trail information.
2. Spend an hour at the Connecticut River Museum
The museum makes a great anchor for a day in Essex, especially if someone in your group wants to understand the river that shaped this place. I still like heading outside afterward just to sit by the waterfront.
3. See the foliage from the water
A boat ride changes your perspective completely. Browse the museum’s RiverQuest and Onrust event calendar for a sailing that actually runs on your date; sunset and specialty trips vary by season.
4. Ride the Essex Steam Train
There’s something wonderfully nostalgic about the train. Check its fall schedule and special experiences in advance; I also think the dinner train is worth doing when offered. We tend to save our family’s most magical train outing for Christmas, but fall is beautiful too.
5. Take in River Road
Drive north from Essex toward Deep River when the foliage starts changing. As the leaves fall, you get more river views through the trees. For a full route, follow my Essex-to-shoreline fall drive.
Chester and East Haddam
6. Have a slow Sunday in Chester
The Chester Sunday Market is one of our favorites. Walk through town afterward; it has a totally different feel from Essex.
7. Order the banana latte at Three Fates
Yes, it’s worth a stop just for the latte. If you need breakfast too, my husband and I love the kielbasa breakfast sandwich at The Villager. Check current menus and hours.
8. Get a beer at Little House Brewing
When there’s no hurry, Little House is an easy Chester afternoon stop. On a warmer fall day, add Honeycone ice cream; for dinner, I love The Village Bistro.
9. Walk the Gillette Castle grounds
The grounds of Gillette Castle State Park are worth the trip for the river views. Go behind the castle and behind the visitor center. I have an extra connection to Gillette’s train: my dad helped spearhead its restoration with others locally. Check tour and visitor center access separately; the grounds can be a lovely outing on their own.
10. Cross the river—when the ferry is running
The Chester–Hadlyme Ferry is one of my favorite tiny adventures. As of September 24, 2026, it is closed until further notice. Check live CTroads alerts. If it remains closed, cross at the Route 82 East Haddam Swing Bridge instead; you can still enjoy Chester and Gillette Castle on the same day.
11. See a show at Goodspeed
A fall day along the river followed by a performance at Goodspeed Musicals is one of those plans that feels like a real occasion. Book ahead and let the show, rather than a packed itinerary, set the pace.
Trails, farms, and the shoreline
12. Hike to Chapman Falls
Devil’s Hopyard State Park has a beautiful waterfall at Chapman Falls. Wear shoes suited to the conditions and check park notices.
13. Pack a picnic for Cockaponset
The Cockaponset State Forest is a beautiful place to slow down over a picnic. Look up the trail and access area you want before you go; it’s a large forest rather than a single stop.
14. Pick apples at Lyman Orchards
A pick-your-own day at Lyman Orchards is one of our family’s fall standards. Check what’s ripe and whether reservations or tickets are required.
15. Make a farm day of Bishop’s Orchards
Bishop’s Orchards is another favorite with the kids. Picking conditions change week to week, which is half the fun if you look before leaving.
16. Go to Clyde’s Cider Mill
Clyde’s is a classic October outing. It’s the kind of place where the cider is the plan; check the current season and opening days.
17. Have coffee and visit the animals at Deep River Farms
We love grabbing a coffee there, sitting on the wooden swing overlooking the pond, and walking out to see the llamas, goats, chickens, and Highland cow. Confirm public hours and animal access before visiting; farms change activities with the season.
18. Walk Hammonasset and stop at Meigs Point
The beach at Hammonasset State Park feels different once summer ends. My kids love the Meigs Point Nature Center, and we enjoy the walk near the rocks. Check center hours before promising it to the kids.
19. See Old Saybrook by the water
Go the long way from downtown Old Saybrook to Saybrook Point, along the causeway and through Fenwick. This is a drive for looking, not rushing. Respect residential streets and posted access rules.
20. Walk Harvey’s Beach at low tide
Harvey’s Beach is my happy place when the tide is out. A warm fall afternoon on the sandbars is one of the reasons I can’t quite let summer go. Check beach parking and access information before visiting.
If you only have one day
I’d choose Essex + Chester for shopping, coffee, and river views; Essex + Gillette Castle for history and a scenic walk; or Essex + Old Saybrook for a beach day with lunch and dinner in town. With kids, choose a farm or the museum and playground rather than trying to drive everywhere. This October family guide has my actual rainy-day backup plan too.
Frequently asked questions
What are the best fall day trips from Essex, CT?
For a short outing, try Chester’s shops and Sunday market or Gillette Castle’s river views. For a longer outing, take the river drive and continue to Old Saybrook’s shoreline. Apple picking at Lyman or Bishop’s, Clyde’s Cider Mill, and Chapman Falls are other favorites.
Are there good fall activities near Essex for kids?
Yes. Orchards, the cider mill, the Connecticut River Museum, the Essex Steam Train, Gillette Castle grounds, Hammonasset, and Essex’s scarecrow walk are all possibilities. Choose by your children’s ages, weather, and the day’s published schedule.
When should I visit for fall foliage near Essex?
The timing varies each year. I like the whole transition: early color, the fuller foliage days, and the later stretch when thinning leaves open up river views. Check a current foliage report close to your trip rather than relying on a fixed peak date.
Make Essex your home base: We’re Grace & Haven, a women’s, baby and kids, and gift boutique at 23 Main Street. Come tell me which outing made your list.
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.
