With the vibe of a European village, Chester blends its town spirit as an artsy community of 3,800 residents with its world-class dining, eclectic shopping and unconventional abundance of ways to tour the area beyond Main Street. Getting around town is actually fun here: There’s more than a half dozen marinas and yacht clubs, a local airport and historic ferry dating back to 1769! The 65ft ferry is a quaint ride and real convenience; The trip itself is a continuation of scenic Route 148, from Chester to Hadlyme.

While best known for its vibrant downtown village shops and restaurants, there are also exceptional pop-up and outdoor shopping events that treasure hunters of all budgets adore: There’s the Town Wide Tag Sale on Saturday of Memorial Day Weekend; the Chester Sunday Market that is held mid-June through mid-Oct; and the Chester Village Holiday Market that runs on Sundays between Thanksgiving and Christmas. 

Chester’s most beloved nature-scapes are the expansive Cockaponset State Forest, Connecticut River vistas and put-in points, and Cedar Lake, which boasts two public beaches surrounded by rolling hills. It’s most unexpected outdoor asset is Camp Hazen, one of New England’s most exceptional summer camps and outdoor education centers. Camp Hazen also offers family programs, including Family Camp Weekends and Mother-Daughter and Father-Son Weekends on select dates in May and Labor Day and Columbus Day holidays; welcoming  (and cooking 90,000 delicious meals!) for 6,000 overnight visitors annually.

Animal lovers, yogis and fiber enthusiasts are all enamored by Chakana Sky Alpacas. Onsite, this farm offers education on the breed and breeding programs, serves as a sanctuary and produces fiber and fiber products. Be sure to check their Morning Yoga with the Alpacas held on select Open Farm Sunday mornings – brought to you by the Inner Sol Yoga Studio.


Chester is a small town with huge love for the arts; it’s home to a number of art museums, theatre and music venues. Explore Leif Nelson Studio & Gallery – also a hopping music venue, plus Chester Gallery, Lori Warner Studio & Gallery, and Norma Terris Theater, home to Goodspeed Musicals. Also, visitors can partake in Chester’s First Fridays at the start of each month; enjoy touring many of these locations that have special events and sales and stay open late.  


Capture fresh fun at the quintessential Chester Sunday Market, snap splash-full memories at Cedar Lake and pause for a moment in time aboard the historic Chester – Hadlyme Ferry on the Connecticut River. 


An indulgence not to miss is Connecticut’s 2019 Restaurant of the Year, Grano Arso. On top of its state awards and national accolades, Chef-Owner Joel Gargano says, “My goal is to prepare dishes that are nourishing, healthful, bright, flavorful, wholesome and honest—brought to the guest with stupendous hospitality.”

But don’t stop just there, you’ll want to spend a few days sipping and savoring local brews and more excellent dining venues. Here’s a short list with big flavor: Little House Brewery, Main Street, River Tavern, Ottos, Pattaconk 1850 Bar & Grill, The Villager, Simons, Wheat Market, Thai Riverside, Hot French Chix, Rustica Ristorante, Moravela’s Pizzeria and Brushmill by the Waterfall.


A cultural heritage tour of note is the summer home of Civil Rights Icon Constance Baker Motley, recently designated as a destination on the Connecticut Freedom Trail. Also, Chester Historical Society’s headquarters of Chester Museum at the Mill just opened in 2010 and features two floors of award-winning exhibits. This 1860s mill overlooks a waterfall near the town center.


The Chester Meeting House has been a wedding destination for centuries while generations of families also love the town’s holiday festivals & parades on Memorial Day, Christmas & Halloween. Alternatively, the little Chester Library is a perfect rainy day activity for all-ages. On sunny days, the ½ mile trail at North Quarter Park is ideal for little feet. The North Quarter Park is also a beautiful creekside bird-watching destination with a ball diamond, a picnic shelter, a playground and there’s Disc Golf coming soon!