Cheshire, CT City Guides



1. Calcagni Associates

City: Cheshire, CT
Category: Relocation
Telephone: (203) 272-1821
Address: 330 S. Main St

Description: There are also offices in Hamden and Wallingford.

2. Watch Factory Restaurant

City: Cheshire, CT
Category: Restaurants
Telephone: (203) 271-1717
Address: 122 Elm St.

Description: This restaurant anchors the Watch Factory Shops here in Cheshire, and features an Austrian menu, which is quite rare in Connecticut. The Central European cuisine by chef Markus Patsch is delightful, with treats like mussels in cream sauce and roasted monkfish. The duck leg is scrumptious, and be sure to split the Gruyère cheese, spaetzle, and crispy onion appetizer. For those preferring a traditional Austrian meal, both the Jaeger and Wiener schnitzels are delicious. Be sure to accompany dinner with a German wine like a Lemberger or Riesling to complete the experience. Their hours can be changeable and they often host large parties, so call ahead and make a reservation. If you come early, wander around the shops and up to the old Cheshire Green to work up an appetite.

3. Funky Monkey

City: Cheshire, CT
Category: Restaurants
Telephone: (203) 439-9161
Address: 130 Elm St.

Description: At first you might think this hangout in the Watch Factory Shops of Cheshire is just a neighborhood hangout, but it is much more. With changing exhibits of local art and musical and comedy events throughout the year, this has become a destination for the locals in the surrounding towns. Unlike most coffee shop and sandwich joints, the Funky Monkey has handpicked beer and wine selections as well. Their delicious wraps and paninis are supplemented by baked goods, quiches, gourmet salads, and fruit smoothies. Try the Funky Monkey BLT, with its jalapeño bacon and avocado. Scrumptious.

4. Sweet Claude’S

City: Cheshire, CT
Category: Restaurants
Telephone: (203) 272-4237
Address: 828 S. Main St.

Description: Sweet Claude’s old Victorian house in Cheshire seems incongruous. You might notice people relaxing on the green hillside under the twisted cherry tree, or the line snaking out the door even in the off-season, and wonder what you’re missing. We’ll tell you. All the ice cream (and hot fudge) is made on the premises, with tempting flavors like toasted almond and cupcake. Their “only for adults” Bailey’s Irish Cream and rum raisin are a delightful change for Mom and Dad. Sit on the porch above the busy Route 10 and wonder why everyone else isn’t stopping, too.

5. Blackie’S Hot Dog Stand

City: Cheshire, CT
Category: Restaurants
Telephone: (203) 699-1819
Address: 2200 Waterbury Rd.
Insider Pick:

Description: Opened in 1928, this classic road-food stand just off Route 84 has ancient signs inside that proclaim No Dancing. But you’d probably be okay if you really wanted to these days. Still, they maintain the strict Catholic tradition and don’t open on Friday or holidays like Easter. But their traditions with food are far more interesting to us. Blackie’s (as in Black Irish) boils their hot dogs in cottonseed oil and then grills them, creating some of the best in the state. Don’t ask for fries, though; they serve only chips. The milk shakes are excellent; get the vanilla one, or a birch beer to go with your dog. The relish is the key, though, a homemade concoction that makes relish haters love the stuff. They even have jars to take home now, so make sure you grab one on your way out.

6. Bovano

City: Cheshire, CT
Category: Shopping
Telephone: (203) 272-3200
Address: 830 S. Main St.

Description: The artisans at Bovano cut shapes and clean copper parts, then enamel them, fusing them with glass elements to create unique decorative sculptures, like different species of birds and dragonflies, flowers and butterflies. These welding and brazing techniques are revered throughout the world, and this is the only place in Connecticut and maybe the US that hand-enamels artwork in this way. The shop also sells other home goods like beautiful lamps, wind chimes, bags, shoes, and unique children’s products. Handmade clocks, paperweights, canes, and bowls are also featured, but it’s the copper/enamel/glass masterpieces that have given Bovano its worldwide reputation. What’s more, they’ve been doing it for over 50 years.

7. Hitchcock-Phillips House And The Heritage Walk

City: Cheshire, CT
Category: Tours & Attractions
Telephone: (203) 272-2574
Address: 43 Church Dr.

Description: Although busy Route 10 passes through the Cheshire town green, it remains startlingly intact. The Heritage Walk takes you around the green with its Civil War monument, past an ancient sycamore tree, and down Main Street past 10 historic buildings from the 18th and 19th centuries. The most impressive are the Abijah Beach Tavern from 1750 and the Foote House from 1767, owned by a prominent family with a governor and a Civil War hero in its ranks. The 1785 Hitchcock-Phillips House, open on Sun in the summer and by appointment, has a fine collection inside, including the traveling desk of president Millard Fillmore and a glass-topped table used by President Grant for his medals. This museum of not only Cheshire but American history contains various paintings, tools, artifacts, and photographs from the last two centuries and beyond. Don’t miss the folding game table used in the White House by presidents from Abraham Lincoln to Harry Truman. You can find a walking tour map on the website.

8. Barker Character, Comic, And Cartoon Museum

City: Cheshire, CT
Category: Tours & Attractions
Telephone: (203) 699-3822
Address: 1188 Highland Ave.

Description: When Herb and Gloria Barker opened this museum to the joys of memory and story, they knew they had one of the largest toy collections in the country, but they didn’t know how much other people would enjoy it. This is so much more than a cartoon museum, you might think it needs a few more additions to its already long name. You will also agree that they need a larger space for the thousands of items. Classic children’s lunch boxes line the walls, and huge Simpsons characters greet you. The museum has first-edition Star Wars figures still in the box, old Looney Tunes puzzles, Pez dispensers, and other nostalgic items that might lead you to believe this museum is more for adults who never grew up than for today’s children. However, the collection keeps growing and includes many current toys, such as Harry Potter items. They have everything from original California Raisins memorabilia to toys from the 19th century. You can also buy original cartoon cels in the gift shop.

9. Roaring Brook Falls

City: Cheshire, CT
Category: Tours & Attractions
Telephone: (203) 271-6670 (Environmental

Description: Kept by the Environmental Commission of Cheshire, this 80-foot waterfall leaps off the plateau in Prospect and is the highest single drop in the state. The trail starts from a small paved lot on Roaring Brook Road, 0.3 mile west from Mountain Road. It’s a suburban setting that hardly seems the place for a dramatic waterfall. But in just a few hundred feet, you’ll reach a viewpoint (there are several to feel out and explore for the best photo) of the falls. Continuing up the orange-blazed trail, you’ll reach the northern section of the Quinnipiac Trail, the oldest blue-blazed in the state. If you hike to the south a mile or so, you’ll cross a road and reach Mount Sanford, an 800-foot mountain with views to the west (don’t worry, you’ve already done most of the uphill work). Go in the spring when the falls are gushing, or in the winter when they are sometimes frozen to the cliff wall.
Back to Connecticut