Source / Robert Jaccoi – Google Maps
Don’t listen to anyone who tries to tell you that summer is wrapping up!
Okay, well, maybe it’s winding down a bit, but there’s still plenty of adventure waiting to be had. And with our precious soak-up-the-sun time officially becoming limited, there’s never been a better excuse to seek out a lesser–known destination for one last-minute summer escape. And who knows? A spontaneous day trip could even turn into a long-standing summer tradition, especially when it comes with scenic landscapes, exciting wildlife, and cascading waterfalls.
Tucked between our favorite city and Connecticut’s bustling capital of Hartford is a lesser-known destination that feels worlds away from the usual summer crowds. With plenty of natural beauty to explore and enough things to see and do to fill an entire day, it’s the kind of place that makes you wonder why you hadn’t heard of it sooner. And the best part? It’s close enough to NYC to make for an easy summer getaway.
Source / Visit Connecticut
What to know: Southbury, CT, The Ultimate Secret Off Interstate 84
Located just 85 miles northeast of Midtown Manhattan, Southbury strikes a balance that is rare along the East Coast corridor: effortless accessibility combined with unhurried small–town charm.
Home to roughly 20,000 residents, this historic community is defined by rolling New England hills, quiet riverfronts, and an authentic farm-to-table spirit.
Southbury stands out for its commitment to land conservation—holding 30-plus parks and nature preserves—alongside a walkable Main Street District listed on the National Register of Historic Places.
Whether you are driving up for a weekend road trip or flying into nearby regional hubs like Tweed-New Haven or Bradley International, Southbury serves as an ideal, traffic-free basecamp for exploring western Connecticut’s Housatonic Valley.
What to do in Southbury: Waterfalls, Bald Eagles, and 18th-Century Architecture
Chase Cascades at Southford Falls State Park: Spanning 169 acres, Southford Falls is Southbury’s outdoor crown jewel. A gentle 2-mile loop leads visitors past a picturesque covered bridge, a historical paper mill dam, and a roaring, tiered waterfall on Eight Mile Brook. Don’t skip climbing the wood-framed observation tower for panoramic views of the forest canopy.
Spot Rare Raptors at Shepaug Eagle Observation Area: Located along the Housatonic River, the hydroelectric station here keeps water from freezing during winter, creating a prime hunting ground for bald eagles, goshawks, and red-tailed hawks. It’s one of the largest wintering eagle spots in New England. Pro tip: Admission is free, but online reservations are required prior to visiting.
Walk History Along Main Street South: Step back into the 18th century on a self-guided architectural tour. Highlights include the red-brick Bullet Hill School (one of America’s oldest continuously used schoolhouses), the Hollister-Romanauskas House, and classic Georgian and Federal-style doorways featuring delicate glass sidelights and ornate porticos.
Take in Lake Zoar Overlooks at Kettletown State Park: Threading along the borders of Southbury and Oxford, Kettletown offers 6 miles of forested hiking trails that open up to dramatic cliffs overlooking Lake Zoar. It’s a prime destination for kayaking, shoreline fishing, and quiet nature photography.
Source / Expedia
Where to eat and drink in Southbury: Mom-and-Pop Diners, Wood-Fired Pies, and More
Laurel Diner: A local institution for classic American breakfast and lunch. The vibe is unapologetically old-school, and their homemade corned beef hash is famous across the county. Note: Bring crisp bills—this legendary spot remains strictly cash-only!
Brunch House 1850: Housed inside a restored 19th-century landmark, this restaurant pairs historical ambiance with a modern menu of artisan paninis, gourmet omelets, and craft espresso drinks. Grab a table on the outdoor patio for peaceful views overlooking the nearby greens.
Julio’s Wood Fired Pizza & Grill: The pioneer of brick-oven pizza in Southbury (serving the town since 1997). Julio’s makes all pizza dough, sauces, and pasta fresh in-house every morning, featuring daily Italian specials highlighting local seasonal produce.
AM Coffee & Co: The ideal morning pitstop for specialty caffeine drinks. Known for sourcing locally roasted beans and fresh regional pastries, it’s also one of the most gluten-free-friendly cafes in the region.
Source / Southbury CT
How to get there from NYC
By Car: Take I-684 N to I-84 E for a 1.5- to 2-hour drive directly into Southbury via Exits 14 or 15.
By Direct Bus: Hop on a Peter Pan bus from Port Authority Bus Terminal straight to the Southbury commuter lot in about 1 hour and 50 minutes.
By Train & Rideshare: Ride Metro-North to Brewster or Waterbury station, then take a 20-minute Uber or Lyft into town.