If you close your eyes and picture a quaint, historic town, that’s Chester.
The Morris County town, which dates back to the 1700s (when it was known as Black River), has its roots in farming—and a number of farms are still in operation today, offering pick-your-own veggies and fruits as a fun fall activity. (Of note: Chester is divided into the Borough, which has a population of 1,675, and the township, with a population of 7,729.)
But the center of the action here is the bustling yet quaint downtown, a lovely stretch of several blocks dotted with funky independent boutiques (no chains here!), great small restaurants, a newly reopened historic hotel and, of course, plenty of interesting people to meet.
WHAT TO DO
Head to Main Street and explore the shops. Favorites include Comfortably Chic for home goods and beautifully framed, affordable art; Dainty Dandelion for custom painted vintage furniture; Black River Candy Shoppe for sweets; &Home for handmade home goods; Chester Country Furnishings for decor and home goods; and Chester Crafts, Collectibles & Antiques for quirky antiques.
Ruth Chodniewicz, founder of Yellow Orchid Co. in Chester, calls the town “my own Stars Hollow,” referencing the charming town where TV’s “Gilmore Girls” is set. Photo: Laura Moss
Stop by the Art Diner, an art studio with drop-in hours and events, plus a delightfully messy Splatter Room. Also visit the chic new storefront for Yellow Orchid Co., an event-planning and floral-design company that also sells funky home items.
Municipal Field, meanwhile, hosts a smattering of townwide events, including the Fall Craft Show September 9-10, concerts, movie screenings and holiday events.
Beyond downtown, visit the stunning Willowwood Arboretum. The gardens are exquisite, and life-size sculptures by Seward Johnson are on display through November 15. Part of Hacklebarney State Park is in Chester; enjoy a hike, then stop at Hacklebarney Farm for cider and pie.
An odd but interesting sight is located in Highlands Ridge Park: more than 700 old and abandoned telephone poles, nicknamed the Telephone Pole Farm. The location is a former testing facility for AT&T.
For apple picking, visit Riamede Farm. On your way out of town, stop at Chester Meat Market; the hot dogs are the stuff of local legend.
Pren Kitchen serves scratch-made comfort food in a very comfortable environment. Photo: Laura Moss
WHERE TO EAT
Buy our September 2023 issue here. Cover photo: Laura Moss
A short drive from downtown is Bill’s Luncheonette, an excellent, family-run joint since 1949. Downtown, options include Pren Kitchen for scratch-made comfort food, Fresco Mexican for tasty Mexican food, and Sally Lunn’s Tea Shoppe & Restaurant for a classy lunch. If you’re in the mood for something sweet, head to Taylor’s Ice Cream Parlor for homemade ice cream or , Crib Bakery for top-notch cookies and cupcakes.
WHERE TO STAY
The historic Publick House Hotel (which dates back to the early 1800s), revamped, renovated, and reopened in January. The hotel features a steak house downstairs and 10 charming suites upstairs; one-bedrooms run $175/night and two-bedrooms are $225. Manager Jennifer Evans says the history of the area is the biggest draw. “Some people say, ‘Put me in the haunted room,’” Evans says. But the bigger question is: Which room?
Want to keep exploring? Check out more of our 12 favorite small towns to visit now.
Comfortably Chic, 47 Main Street; Dainty Dandelion, 58 Main Street; Black River Candy Shoppe, 44 Main Street; &Home, 54 Main Street; Chester Country Furnishings, 60 Main Street; Chester Crafts, Collectibles & Antiques, 28 Main Street; Art Diner, 18 Main Street; Yellow Orchid Co., 38 Main Street; Willowwood Arboretum, 300 Longview Road; Hacklebarney Farm, 104 State Park Road; Highlands Ridge Park, Riamede Farm, 122 Oakdale Road; Chester Meat Market, 27 W. Main Street; Bill’s Luncheonette, 455 North Road; Pren Kitchen, 52 Main Street; Fresco Mexican, 137 E. Main Street; Sally Lunn’s Tea Shoppe & Restaurant, 15 Perry Street; Taylor’s Ice Cream Parlor, 18 Main Street; Crib Bakery, 57 Main Street; Publick House Hotel, 111 Main Street
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