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Tucked into the rolling hills of southern Morris County, Chester is one of those towns that feels frozen in the best possible way. Brick sidewalks, creaky front porches, and well preserved storefronts give historic Main Street a pure Americana feel, while the farms and parks that surround the borough keep it tied to its agricultural roots. Fall is Chester’s busiest and best season, with corn mazes, pick-your-own farms and Main Street shop events stacked into every weekend. Whether you have a full day or just an afternoon, here is how the locals spend their time in Chester.
Stroll Historic Main Street
Downtown Chester is built for wandering. Historic Chester is home to more than 80 boutique shops, from antique dealers and home decor boutiques to jewelers, candy stores, and specialty food merchants. It is nearly impossible to walk past the storefronts without stepping inside. Anyone with a sweet tooth should stop into the Black River Candy Shoppe at 44 Main Street, with its wall of Pez dispensers and jars of nostalgic favorites. If you are in the mood for bigger-name retail, the Streets of Chester shopping center sits just off Route 206 with familiar stores a short drive from downtown.
Cool Off With Homemade Ice Cream
No trip to Chester is complete without a stop at Taylor’s Ice Cream Parlor at 18 Main Street, an old-fashioned parlor scooping dozens of flavors of homemade ice cream. It is a summer institution, and the line out the door on a warm evening is part of the charm, but a cone after a fall afternoon on Main Street works just as well.
Spend a Day at Alstede Farms
Just outside the downtown, Alstede Farms is a 600-acre working farm and one of the most beloved family destinations in Morris County. You can pick your own fruits, vegetables, and flowers through the seasons, visit the farm animals, browse the farm store, and grab a scoop of homemade ice cream or a cider donut. In fall, pick-your-own runs in timed slots, and Harvest Moon Nights add a nighttime corn maze, hayrides and bonfires from 6 to 10 p.m. on weekends through October 31.
Corn Mazes and Fall Farms
Chester is the heart of Morris County’s fall farm country. Stony Hill Farms on North Road runs its corn maze daily through November 1, with a 2026 “NJ 250” theme, and tickets are sold online only. Riamede Farm on Oakdale Road is open Wednesday through Monday through November 1 for apples, pumpkins and flowers, with hay wagons and pony rides on weekends. For more farms around the county, see our guide to pumpkin picking and corn mazes in Morris County.
Step Back in Time at the Cooper Gristmill
For a taste of local history, the Cooper Gristmill at 66 Route 24 is worth the stop. Built in 1826 and run today by the Morris County Park Commission, it is the only restored water-powered mill in New Jersey, and it marks its 200th anniversary this year. Through October, the mill is open Fridays and Sundays from 10 a.m. to 3 p.m., and admission includes a guided tour by the miller showing how grain was once ground into flour and cornmeal. The 14-acre site along the Black River has trailheads and quiet spots for a streamside picnic.
Get Outside at Hacklebarney State Park
Chester is surrounded by green. Hacklebarney State Park is the crown jewel, a rugged and scenic park where the Black River tumbles past boulders and hemlocks, with waterfalls along the trails. Fall foliage makes it one of the prettiest hikes in the county. For something gentler, the Kay Environmental Center offers free trails through meadows and a hemlock gorge, and Chubb Park on Route 24 has open fields, a pond and access to Patriots’ Path.
Fall Events on Main Street
Chester’s shops keep the calendar full this fall. Highlights from the Historic Chester events calendar include a Halloween pet costume contest at Winky’s Pet Boutique on Saturday, October 17, Witches Night Out at Rebel Sheep Wine Co. on Friday, October 23, and Pies and Pours at Rebel Sheep on November 14 and 15.
Make a Day of It
That is the beauty of Chester. History, small-town shopping, farm-fresh food, and real wilderness all sit within a few minutes of one another. Pair a morning of hiking with an afternoon on Main Street and a scoop of ice cream to finish, and you have a classic Morris County day. Hungry after all that exploring? See our guide to the best restaurants in Chester, and for more ideas this season browse our guide to fall festivals and fairs in Morris County.
Chester is one of 39 towns here, and every one of them is worth a Saturday. For the whole county in one place, read the free Morris County Guide, our seasonal digital magazine covering restaurants, shopping, downtowns, and things to do in every town.
Cover: Shop Morris County.
More From Chester
Two more Chester stories: the Rose Squared Chester Craft Show and Chester Township marking 250 years with a free all day celebration.
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