Connecticut Fall Foliage Drive
Hidden in the heart of Litchfield County is the crossroads village of New Preston, perched above a 40-foot waterfall on the Aspetuck River. Just north of here you'll find Lake Waramaug, nestled in the rolling foothills and Mt. Tom, both ablaze with rich color every fall.
Start in New Milford and stroll along historic Main Street. Here you'll find New England's longest green and many shops, galleries, and restaurants within a short walk. Hop in the car and drive south on Main Street, then turn left to head north on wooded Route 202. About 4 miles north of the town green is the Silo at Hunt Hill Farm Trust. The former property of the late Skitch Henderson, onetime music director of NBC and the New York Pops, consists of a gallery, cooking school, and gift store housed in the buildings of two farms dating to the 1700s. Continue north on Route 202 to the junction of Route 45 and follow signs for Lake Waramaug.
Route 45 will bring you through the tiny village center of New Preston; stop here for a bit of shopping at Dawn Hill Antiques. Take 45 north and follow signs for Lake Waramaug. The 8-mile drive around the lake is stunning in autumn with the fiery foliage of the red maples, rusty brown oaks, and yellow birches reflected in the water. The beach area of Lake Waramaug State Park (about halfway around the lake) is a great place for a picnic, or perhaps even a quick dip on a warm fall day. Hopkins Vineyard is open daily for wine tasting; head to their Hayloft Wine Bar to enjoy a glass of wine and the spectacular lake views.
After completing a loop of Lake Waramaug, head back to Route 202 North toward Litchfield. Another excellent leaf-peeping locale is Mt. Tom State Park, about 3 miles or so from the junction of Routes 45 and 202. Here you can hike the mile-long trail to the summit and climb to the top of a stone tower that provides 360-degree views of the countryside's colors—the vibrant magenta-reds of the sugar maples are always among the most dazzling. After your hike, continue north on Route 202, ending your journey in the quintessential New England town of Litchfield. Peruse the shops and galleries in the town center and end the day with a dinner at the chic West Street Grill.
It's only about 30 miles from New Milford to the center of Litchfield, but with stops at the Silo at Hunt Hill, Lake Waramaug, and Mt. Tom you could easily spend half the day enjoying the scenery.
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