Food by the Trailhead: Where to Eat Near the Region's Most Popular Hikes

Photo by Rebecca Bloomfield

A good hike deserves a good meal on either end of it—something to fuel the climb, something to celebrate the descent. That can look like a general store that's outlasted three names on its sign, a converted motel, a soft-serve stand where half the county ends up trading gossip in the parking lot.

Some of the spots below sit close enough to a trailhead that hikers walk in still wearing their packs; others are a short drive into the nearest village, all are the kind of pitstop that turns a morning on the mountain into a full day out. Either way, these spots are feeding people who've just spent a few hours on their feet, or treating the ones about to. What follows is a guide for just four of the region's most-hiked trails, and the places nearby for quality eats. 

Columbia County: Bash Bish Falls

Bash Bish is the most-hiked trail in Columbia County: a short, easy out-and-back off Route 344 in Taconic State Park's Copake Falls area that delivers the tallest single-drop waterfall in Massachusetts, right on the New York-Massachusetts line.

Copake General Store

171 County Route 7A, Copake, NY 12516

This general store has become a destination in its own right. When RI visited a few years back, the place—then newly reopened after a previous run as Copake Front Porch—was "packed to the rafters on a Saturday," with a jazz brunch crowd and turkey meatball sliders "flying out of the kitchen like seagulls." That energy remains alongside coffee, hardware odds and ends, and local produce, the deli counter turns out sandwiches like the Serge (turkey, local bacon, cheddar, and a Zghug herb sauce made by nearby Serevan) and the Wild Child (roast beef, cheddar, pea shoots, and horseradish)—good for the porch, or to pack for the trail. Open 9am to 6pm most days, 9am to 3pm Sundays, closed Wednesdays.

North Star

7519 State Route 22, Copake, NY 12516

The North Star, the restaurant inside The Alander, the boutique lodge that replaced the old Johanna's Motel, has become a reliable sit-down option for the outdoorsy. Co-owner Reid Kendall says the restaurant wasn't originally a part of the plan—the property simply came with a bar and a commercial kitchen already in place—but he and co-owner Jason Seiler decided to build a seafood-forward, New American menu around wanting to "welcome the whole community," not just overnight guests. The menu has included a beef carpaccio with garlic herb aioli, arugula, parmesan, and a lemon vinaigrette to start. There are fire pits outside for whoever's not ready to call it a night.

Dutchess County: Poets' Walk Park

In the northern half of the county, Poets' Walk in Red Hook is the region's most popular easy hike: a flat, roughly two-mile loop through meadows and "outdoor rooms" designed in 1849, ending at a gazebo with sweeping Hudson River and Catskills views. Washington Irving is said to have found inspiration for "Rip Van Winkle" wandering the grounds.

Bliss Juice + Cafe

7501 N Broadway, Red Hook, NY 12571

A cold-pressed juice and smoothie bar right in the center of the village—exactly the kind of pre-hike fuel for a breezy stroll through Poets' Walk's meadows. Owner Annie Sullivan bought the original, much smaller Bliss at just 22-years-old; five years later she’s moved it into a bigger, teal-walled space at the crossroads of Broadway and Market Street. The menu includes smoothie bowls, waffles, cold-pressed juices, grab-and-go salads, organic coffee and matcha, and build-your-own juice cleanses. "I want Bliss to be an oasis," she says, describing a place where customers can slow down and feel good about what they're eating.

Holy Cow

7270 S Broadway, Red Hook, NY 12571

After a hike is the best time for a well-earned dessert! Holy Cow is a soft-serve and ice cream stand at Hardscrabble Plaza that RI has called "a marvel of delicious efficiency," run by a tight staff of grandmothers, mothers, and daughters. The menu covers soft serve, hard ice cream, sundaes, shakes, and ice cream cakes, but the shop’s oddest beloved specialty is the "udder"—a scoop of ice cream stuffed into a cupcake wrapper, sold by the box to kids. As the udders warm in their little grubby hands they melt faster than can be eaten. It’s a strange tradition only native Red Hookers ever truly understand. Everyone eats at the nearby picnic tables or the parking lot, which locals will tell you is where you end up meeting half the town.

Berkshire County: Monument Mountain

Monument Mountain, just off Route 7 between Great Barrington and Stockbridge, is the Berkshires' signature short hike: a 2.5-mile loop up the Hickey and Mohican Monument trails to ledges with views across the Housatonic River Valley, made famous by the 1850 picnic hike where Nathaniel Hawthorne and Herman Melville reportedly got the conversation going that led to the writing of “Moby-Dick.”

Berkshire Mountain Bakery

367 Park Street, Housatonic, MA 01236

A short detour into neighboring Housatonic, to the bakery's red-brick headquarters, for sourdough that's been the standard-bearer in the region for decades: ciabatta, spelt pizza crusts, and loaves sold alongside take-and-bake pizza for later. Founder Richard Bourdon, who learned his craft in Holland, is exacting even about ingredients most people never think twice about—describing the hunt for pure almond paste for one holiday recipe as "next to impossible." That fanaticism has led to the creation of bread worth hiking for.

Pleasant and Main

1063 Main Street, Housatonic, MA 01236

Right in the same small village as the bakery, Pleasant and Main is a cafe-slash-general-store run by Craig Bero, who spent 35 years in Manhattan's restaurant scene—most recently running the Cosmopolitan Café in Tribeca—before packing up his collection of antiques and fishing gear and setting up in Housatonic. RI’s previous review called him "a generous and convincing soul," and the dining room, lined with his own antiques, certainly conveys that vibe. The menu includes veggie quiche, eggs Florentine, ratatouille crepes, and a rotating community supper menu that might mean beef pot roast one week and lamb shepherd's pie the next. Currently open Wednesday through Sunday, 8:30am to 3pm, with dinner service added Thursday through Saturday evenings; closed Monday and Tuesday.

Litchfield County: The Appalachian Trail at Falls Village, and Kent Falls

Litchfield County splits its hiking crowds in two directions: the Appalachian Trail corridor through Falls Village and Salisbury, which includes the climb up Bear Mountain, Connecticut's highest peak at 2,316 feet, and Kent Falls State Park, an easier, family-friendly waterfall walk a few miles south.

Off The Trail Cafe

107 Main Street, Falls Village, CT 06031

A cafe built explicitly around its location on the Appalachian Trail, down to the menu. Owners Liz and Howie Ives opened it in 2025 after a Memorial Day soft launch fueled by donated cookies and lemonade from neighbors. The menu leans into trail slang: the Cobb Knocker Salad is named for the hiker who clears a given stretch of trail each morning, and there's a Blaze Burger and a Trail Magic Salad alongside it, plus breakfast sandwiches, coffee from Barrington Coffee Roasting Co., and pastries from Hannah's Donuts. Order at the counter, then take it outside to eat at a table or on foot as you hit the trail.

Ore Hill & Swyft

3 Maple Street, Kent, CT 06757

A pair of restaurants sharing one restored 1781 building near the corner of Main and Maple, a few minutes' drive from the falls: Swyft is the casual tavern side, known for Neapolitan-style wood-fired pizza and shareable plates; Ore Hill is the more intimate tasting-menu side next door. Both opened together under chef Joel Viehland and philanthropist Anne Bass in 2017 and 2018, though Viehland has since moved on and Bass passed away in 2020. Today the kitchen operates under culinary director Tyler Anderson, a James Beard nominee and "Top Chef" alum, alongside executive chef Ryan Connelly—both drawing ingredients and inspiration from Rock Cobble Farm, the 1,000-acre farm Bass founded a few miles away in South Kent, which still supplies both restaurants' produce, beef, and dairy.

Four counties, four trail systems, eight places to eat—consider it a start. If your favorite trailhead spot didn't make the list, let us know; a guide like this is never really finished.