Explore Connecticut's Litchfield Hills This Fall

Nestled in Connecticut’s rugged Litchfield Hills, the town of Kent is the postcard-perfect image of rural Southern New England. From its charming center at the intersection of US-7 and CT-341, bucolic farmland gives way to dense second-growth forests, rocky hillsides, and pristine waterways—all a study in contrast to the densely populated suburban tableau that the Nutmeg State typically evokes.

What local hikers, trail runners, climbers, and paddlers already know though, is that Kent is more than just a pretty face. Miles of trails, awesome climbing, and plenty of water—both technical and flat—make Kent a full-value day trip. Throw in some excellent restaurants and a destination-worthy brewery, and you’ve got yourself a fine spot for a long weekend.

Hiking and Trail Running

From hilltop to hollow, Kent’s state parks, forests, and private land trusts provide access to miles and miles of high-quality trail fit for hikers and runners of all abilities.

The centerpiece, of course, is the venerable Appalachian Trail. 51 of the AT’s 2,190 miles run through Connecticut’s Litchfield Hills offering some of the loveliest low-elevation day hiking and backpacking options in the northeast. If you’re looking for an easy and scenic stroll, head south from Bull’s Bridge to Ten Mile Hill (4.5 miles, out-and-back), taking in a 19th-century covered bridge and a beautiful section of the Housatonic River along the way. For something a bit more challenging, head south from the Saint John’s Ledges trailhead on River Road, traversing Fuller Mountain, Caleb Peak, and Saint John’s Ledges while you catch views on your way to the AT’s junction with CT-341 (4.3 miles, one-way). Looking to fill your weekend? Just north of Kent, in Sharon, the AT–Mohawk Loop (39.4 miles, loop), is an excellent backpacking route that connects the Appalachian trails of the past and present—today’s Mohawk Trail actually traces the original path of the AT before it was rerouted in the 1970’s.

The AT isn’t the only game in town though. Just around the corner, Macedonia Brook State Park boasts an impressive network of trails that offer a not-so subtle reminder that “low-elevation” doesn’t always mean “easy.” Varied terrain, outstanding views, and a climactic rock scramble characterize the Macedonia Ridge Trail—a part of Connecticut’s Blue-blazed Trail Network and one of the state’s finest—as it works its way up and over Cobble Mountain (6.4 miles, loop).

A few miles northeast, Kent Falls State Park and its dramatic, stepped, eponymous cascade drops over 250 feet as it flows into the Housatonic River. Linking the Park Path up with the Red and Yellow Trails makes for a lovely, easy hike up and around the falls (1.5 miles, loop).

Climbing

Connecticut climbing has a reputation for short routes, steep traprock ridges, and incredible sandbags, but Saint John’s Ledges, rising above the Housatonic River in Kent, offers climbers a bit of a diversion: slab. Right along the Appalachian Trail, a quarter mile in from the trailhead parking area on River Road, are the Upper Ledges, a long stretch of friction slab reaching well over 100 feet high in some places.

There’s a good range of difficulty but the majority of lines register as solid, enjoyable moderates with a mix of heady slab moves and jammable cracks—and though some are leadable, protection can be sparse (or non-existent), and top-rope is generally the order of the day. A 60-meter rope alone won’t do it on some routes so be sure to bring a 70 or plenty of static line to build anchors with. Everything is east-facing, and the top half of the Upper Ledges are sunny and warm in the morning, so climbing here can comfortably extend late into the season. Must-do’s include Half Bling (5.8+), Falling Bodies (5.6), and the excellent Trail Magic (5.9-).

There are a handful of areas, and a good amount of climbable terrain, at Saint John’s in addition to the Upper Ledges, including the Lower Ledges, a short, beginner-friendly cliff just off the trailhead parking area. With a pair of super-easy routes like Wilderness Crack (5.3) and Try (5.2), this is an excellent spot for first-time climbers—and if its popularity with groups and classes is any indication, the Lower Ledges may well be the best such area in the state. There is a little bit of something for everyone here though, and more experienced climbers headed for the Upper Ledges will enjoy a change of pace (and some shade) on stout face climbs like The Graduate (5.10-).

Paddling

From its headwaters in Massachusetts’ Berkshire Mountains, the Housatonic River travels 149 miles on its course to Long Island Sound, effectively halving the town of Kent from northeast to southwest in the process. Like the surrounding hills, the Housatonic is emblematic of Connecticut’s Northwest Corner—it’s also one of the finest destinations in the east to fisherman and kayakers alike. The river moves quickly and can be technical at several points, the most noteworthy of which is the Staircase, an obstacle just south of Bull’s Bridge, that heralds rapids up to Class V when the water’s high.

Those seeking gentler waters need look no further than Lake Waramaug State Park. Situated on the border of Kent, Warren, and New Preston, Lake Waramaug is a gorgeous lake in a stunning setting—absolutely perfect for an early morning paddle. The state park also has an adjoining campground, a great spot if you’re in for more than a daytrip.

Eating and Drinking

For a small town, Kent does really well on the food and drink. Get started in the heart of town at Swyft, a cool little joint in a restored 18th-century home that serves up modern, seasonal fare alongside a robust tap list. A local draft and one of their wood-fired, Neapolitan-style pizzas tend to hit the spot after a big day on the trail or at the crag.

No trip to Kent is complete without grabbing a beer at Kent Falls Brewing Company. Located in Kent Hollow, just a hop, skip, and a jump from Lake Waramaug, Kent Falls Brewing Company is a brewery on a working farm specializing in locally sourced ingredients. Their beer menu is wide-ranging, ever changing, and always excellent and the setting is as bucolic rural Connecticut as it gets.