What to Do in Lenox

A NEW LOCAL’S OPINIONATED GUIDE ON WHAT’S WORTH YOUR TIME, TASTE, AND CURIOSITY IN LENOX 

By Heather Dunhill

Allow me to introduce myself: I'm Heather Dunhill, three years into my Berkshires chapter, having swapped Sarasota’s beaches for these rolling hills. That makes the region a fresh adventure—think exploring Lenox and neighboring towns, each with a knack for storybook charm. 

My husband, Ted, and I have become professional wanderers, following breadcrumbs from local Instagram feeds, tips whispered by year-rounders, dispatches from periodicals, and overheard to-dos at Boema Pizzeria’s lively bar. 

Top row, Honeychurch Home (Courtesy of Honeychurch Home). Middle row, from left, Shots Café and Lykke Living. (Gregory Cherin) Bottom row, The Fernery by design menagerie (Gregory Cherin). 

First pro tip: Boema’s wood-fired, Neapolitan pies, blistered in a 900-degree oven at 84 Main Street, have ruined us for just about any other pizza. If finger food is your love language, note this: Brava’s wings at 65 Church Street are a flavor adventure worth tracking, with a different sauce every day. And for a lunchtime flex, Bistro Zinc’s fried oyster Caesar—crispy, briny, unapologetically decadent—shows up on both lunch and dinner menus at 56 Church Street. Eyes up—you never know who’ll be lingering in the corners at this local favorite. 

Important to remember: Lenox doesn’t hit pause after the leaves have dropped. The town never truly dims, no matter how cold it gets—there’s always a glow, and always a reason to step out, even when sweater weather turns into full parka season. You can take leisurely laps up and down Main Street without dodging packs of weekenders and pop in for something flaky or savory before a Tanglewood Learning Institute salon or Linde Center concert or settle in for a witty show or costumed reading at Shakespeare and Company. Off-season, but not off your list. 

So, yes, this newcomer comes with strong opinions on where I’d actually send you, if asked. Here are my unfiltered picks for everything Lenox.

The Bookstore

11 Housatonic Street • 413-637-3390

If you do nothing else in Lenox, make it a pilgrimage to The Bookstore—a fixture that’s been fueling the town’s literary heartbeat since the days when Alice’s Restaurant was bustling. Proprietor Matt Tannenbaum—ever the raconteur—will tell you it’s been “serving the community since last Tuesday.” Regulars and newcomers drift in not just for novels, but for the pleasure of swapping suggestions, catching Matt mid-verse as he recites a daily poem, or soaking up a joke spun from behind the counter. For your tote, consider a copy of What Goes on Inside a Beaver Pond? by local talent Becky Cushing Gop, director of Mass Audubon West. Call it a crash course in woodland neighbors for the uninitiated, or a clever keepsake (it’s charming and educational, promise). It’s also a just-right find for any pint-sized readers on your list.

The Fernery 

by design menagerie

48 Main Street, Suite 3 • 413-551-7107

Step inside The Fernery and find yourself in a botanical haven—an airy, design-forward space curated with beautifully utilitarian objects and wardrobe pieces; some destined for forever status, quietly promising they’ll age like the very best kind of friend. The selection, items crafted by makers from around the world, reflects an ethos of sustainable artistry. Names like Pas de Calais, MOMA, Gabriele Frantzen, and Antipast—these whimsical socks are the handiwork of Japanese creatives. They made me into one of those people with an accidental sock collection.

Honeychurch Home

35 Church Street • 413-551-7061

Honeychurch Home is quiet luxury, realized. For me, this boutique is an instant escape—like stepping inside a chic yet inviting European home, thoughtfully collected and layered with artistry and comfort. The boutique features an inspiring mix of indoor and outdoor décor, clothing, Parisian linens, luxe garden wares, and handpicked gifts, each selected for timeless appeal. Expect to find enduring classics from SCAPA, Astier de Villatte, Trudon, and Frances Palmer Pottery. Every piece here reflects a beautifully clear vision: daily living, made effortlessly special. 

Lenox Coffee

52A Main Street • 413-637-1606

Just steps from The Fernery’s front door, tucked into a charming house, sits Lenox Coffee—home to locally roasted beans and bona fide baristas. The chai latte with frothy almond milk is the order that keeps me coming back: made from scratch with loose tea and warming spices, it’s an aromatic, cozy sipper that’s converted more than a few coffee loyalists to something new. Bring your latest read or your laptop and settle in—this is the kind of place designed for lingering. The doors are open every day until 4 p.m., making that second cup less of a temptation and more of a given.

Lenox Library

18 Main Street • 413-637-0197

Once the Berkshire County Courthouse, the 19th-century Greek Revival building housing the Lenox Library still impresses with its stately Ionic columns and elegant cupola. But this is more than a bibliotheca. It once held the town’s first telephone switchboard and echoes with civic pride and heritage. Today, it’s a quiet hub. The entryway is where locals post happenings. Inside, you can plug your phone in at the recharging station, then settle into a wingback armchair with the day’s paper. Don’t miss the Book Nook, my reliable spot for discounted reads I never knew I needed. Have books to spare? The library welcomes year-round donations.

Lykke Living

27 Church Street • 413-644-6685

This boutique is the brick-and-mortar version of lykke (pronounced LU-kah)—that Danish notion of deep contentment, well-being, and everyday warmth. Picture a shop that’s done all the joyful hunting for you, lining up treasures for yourself and others at prices that turn little luxuries into everyday treats. Be sure to take in my new favorite, the Palo Santo soap—it’s a fresh, woody, and herbal scent. Not to be missed are the delectable provisions, Parisian hand-blown glassware, and playful plush animals from Australia for the kiddos, each with its own backstory. 

Shear Design Salon 

25 Church Street • 413-637-2662 

I’m often asked for a salon recommendation, and the answer comes easily. As a longtime Aveda devotee, Shear Design was a natural fit. But it’s the talent—and the real warmth—of the stylists that turned me from a one-time visitor into a full-on regular. Stop in for a chance to win the salon's monthly drawing, which is a playful nod to the “guess the candies in the jar” tradition from grade school. The difference? Now, the winning guess scores an Aveda gift box worth $300 or more, not just bragging rights and a single lollipop. (No complaints, but it’s a clear upgrade.) 

Shots Café 

27 Housatonic Street • 413-637-9820 

Open Tuesday through Saturday, this continental-style café takes pride in serving local Berkshire favorites: hearty breads from Berkshire Mountain Bakery, freshly roasted coffee from No. Six Depot, ice cream from High Lawn Farm and SoCo, and all-natural treats from The Berkshire Dog. The menu brims with fresh-baked pastries, inventive breakfast and lunch dishes—such as crepes, paninis, and quiche—plus ever-changing daily specials. On chilly days, I can’t pass up a mug of one of their warm seasonal drinks, such as hot apple cider. Adding the caramel apple butter topping is a splurge, but it’s as delightful as it sounds. 

What a Gift 

68 Main Street • 413-551-7424 

Step inside, and you’ll find the quintessential gift shop. Trinkets you won’t see everywhere else: dainty earrings sealed in glass vials (with actual cork stoppers, thank you), Lost Horizons hats and gloves hand-knit from New Zealand wool, each blooming with charm. There are watercolor workbooks from Emily Lex Studio for channeling your inner artist, an armoire of gifts for kids, and shelves lined with cards that are as witty as they are heartfelt. My personal go-to gift? A miniature canned candle—each one wrapped with a meaningful quote that’s a balm to the soul.