What are the ingredients for a memorable fall road trip? Great leaf peeping? Clear mountain air? Farm stands for easy access to cider donuts? You can check all those boxes on this weekend's escape because we're heading to the O.G. of American road trips: the Berkshire Mountains of Massachusetts. This destination about two hours west of Boston has been luring roadtrippers in search of the best scenic and rustic qualities New England has to offer since the Mohawk Trail — one of the country’s first scenic byways — opened in 1914.

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But before we dive in, let’s get a handle on the geography. The Berkshires — or "The Shire" as some locals call it — encompasses a huge area that hugs the western border of Massachusetts. In future issues of The WeekEnder, we’ll head to South County, which is known for its Gilded Age opulence and refined cultural festivals like Tanglewood. But for this weekend’s getaway, we’re going to North County, a region that’s a bit less discovered but just as enticing.

In this part of Massachusetts, the mountains are bigger, the pace is slower, and the opportunities for COVID-safe social distancing are endless. Plus, there’s serious art in these hills, as well as hotels with major design cred and an emerging culinary scene. Most of the action is based in post-industrial North Adams and the crunchy college town of Williamstown. But you’ll also find plenty of nature for easy walks and some of the best leaf-peeping in the country, if not the world. Let's get started.

Get there

3+ hours from Midtown Manhattan to Williamstown, Massachusetts, the heart of the Northern Berkshires.

Pit stop

Stop by the 1953 West Taghkanic Diner in Ancram, New York, a vintage diner now run by Kristopher Schram, a globally-trained chef.

Listen to

• That Berkshire Podcast: An insider’s view of what it’s like to live in the Berkshires.

• Ode to Joy: The latest album from Wilco, whose members have deep Berkshires connections.

Don't forget

• A COVID-safe face mask and hand sanitizer

• Comfortable hiking boots for hitting the trails

• Casual threads: Jeans and a warm fleece are the norm

Map of the area

1. Mount Greylock

2. Jiminy Peak

3. Clarksburg State Park

4. TOURISTS

5. Guest House at Field Farm

6. MASS MoCA

7. Clark Art Institute

8. Cricket Creek Farm

9. Mezze Bistro + Bar

10. Old Forge

Many places have updated safety procedures due to COVID-19 restrictions and reopenings. Visit our Travel Safe landing page to learn more.

For New York state specific information, visit the official Massachusetts COVID-19 Information Page.

Mount Greylock

Towering above North Adams and Williamstown is Mount Greylock — the highest point in Massachusetts and catnip for leaf-peepers. For a kaleidoscope of colors and views stretching to Vermont, drive right to the peak. “There are so many trails, and it has inspired writers through the centuries such as Melville when he wrote Moby Dick,” says Anastasia Stanmeyer, editor-in-chief of Berkshire Magazine. “Have a drink or a bite at Bascom Lodge at the top.”

Want more fall foliage?

Jiminy Peak: The largest ski area in Massachusetts has an aerial park with a mountain coaster for zipping through the vibrant trees. “You can even take the chairlift up — perfect for kids and tired travelers,” says Sarah Eustis, CEO of Main Street Hospitality Group, which runs The Porches Inn at MASS MoCA, as well as other hotels and restaurants in the area.

Clarksburg State Park: Between North Adams and the Vermont border is this 368-acre forest with a trail that goes around a pond. “It’s a stunning watering hole in the middle of the woods — best in the morning when the fog comes off the water,” says Jessica Sweeney, founder of Common Folk Artist Collective. “There’s also fall camping if you want to wake up in the middle of the foliage.”

Get lost. Seriously, just drive around. “The scenery is so grand in the northern Berkshires that you don’t necessarily need a destination,” says local cookbook author Alana Chernila. “Grab a picnic from the self-serve store at Cricket Creek Farm in Williamstown and just take a road that seems like it’s going up. You’re guaranteed to find an amazing view.”

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TOURISTS

What do you get when you combine a bassist for an indie-rock band (Wilco), a James Beard Award-winning chef, a craft brewer, and the founder of Brooklyn Magazine? TOURISTS, an eco-chic resort inspired by midcentury motor lodges set on the river between Williamstown and North Adams. But this isn’t just another overhauled motel: TOURISTS was designed by a protégé of the architect who created MASS MoCA. It also has a speakeasy bar in an 1813 farmhouse, miles of hiking trails, its own radio station, and — ideal for COVID-era stays — personal fire pits.

Don’t Miss: This fall, the hotel is leading foliage hikes, orchard walks, and apple-picking expeditions. It’s also partnering with the local Berkshires Cider Project to teach guests how to make their own hard cider.

Honorable hotel mentions

For Instagrammers: The Porches Inn at MASS MoCA. A row of 19th-century former millworker houses that’s been converted into a boutique hotel across from the contemporary-art museum in North Adams.

For Collegiate Types: Williams Inn. A modern take on a New England farmhouse filled with pieces by local artists and a farm-to-fork restaurant.

For Nature Lovers: Guest House at Field Farm. Six-room Bauhaus-inspired bed & breakfast set on 316 acres of conserved land in Williamstown with miles of walking trails.

For a Cheap Sleep: Bascom Lodge. Rustic mountaintop lodge with affordable rooms catering to hikers and budget travelers. The views can’t be beat.

Arts and culture

Scattered throughout the mountains of North County are two of the most significant art institutions in the country. We know navigating museums — especially ones with world-class collections like these — can be challenging when you only have a weekend, so we did the homework for you.

Post-industrial art: MASS MoCA

What it is: One of the largest contemporary-art museums in the U.S., the Massachusetts Museum of Contemporary Art, a.k.a. MASS MoCA, stretches across 16 acres of former mill and factory buildings in North Adams.

Names you’ll recognize: Legends like Louise Bourgeois and Jenny Holzer, alongside up-and-coming artists.

Your Instagram moment: Sol LeWitt: A Wall Drawing Retrospective, with 105 large-scale drawings installed on walls specially built for the pieces according to the artist's own specs.

Not to miss: Perfectly Clear — dazzling displays of light and space by James Turrell (reservations are required).

The discovery: In Harmonocity, The Tonal Walkway, a sound art installation by Julianne Swartz.

The takeaway: Quirky Blue Q pouches and totes made by a local design collective from 95% recycled materials — available at the MASS MoCA gift shop, a store that’s as cool as the museum itself.

Art in a natural setting: Clark Art Institute

What it is: In 1955, the trailblazing Clark Art Institute opened in Williamstown to house the private collection of globetrotting art enthusiasts Francine and Sterling Clark, heir to the Singer sewing machine fortune.

Names you’ll recognize: Heavy hitters like Winslow Homer, John Singer Sargent, and Renoir.

Your Instagram moment: Ground/work, a series of site-specific installations spread across the museum’s 140 acres of COVID-friendly open spaces. It’s been in the works for three years, but the exhibition couldn’t be better timed.

Not to miss: Degas’s Little Dancer Aged Fourteen, which has her own gallery. The famous piece was purchased by the Clarks themselves at an estate sale after the artist’s death.

The discovery: Crystal, a large-scale sculpture by contemporary artist Thomas Schütte that viewers can enter to see a perfectly framed view of the surrounding mountains and valley.

The takeaway: Clark Honey, collected in small batches from the museum’s own rooftop bee colony and flavored with the surrounding meadows — available at The Clark Store.

Want more art?

Common Folk Artist Collective, a grass-roots gallery in North Adams that showcases local talent. While it has been closed during COVID, Common Folk is scheduled to reopen in mid-October; in the meantime, its online store sells some of the best souvenirs in town — “CSA” boxes curated by members and filled with local arts and crafts instead of produce.

Northern Berkshires Art Outside Tour, a series of COVID-friendly self-guided walking and biking tours throughout the grounds of the Williams College Museum of Art — an excellent art institution that is closed due to COVID — as well as other open-air art spaces in the area.

Farm-fresh finds

The fertile soils of the Berkshires have supported a long agricultural history stretching as far back as the 1700’s. Here are four delicious North County addresses to have on your radar:

Artisanal cheese: Cricket Creek Farm, a grass-fed dairy farm in Williamstown renowned for its award-winning Maggie’s Round, a raw-milk cheese inspired by the Italian Alps.

Apples: Lakeview Orchard, a pick-your-own farm in Lanesborough with 23 varieties of apples.

Pumpkins and maple syrup: Ioka Valley Farm in Hancock, where fall means a pumpkin patch and a petting zoo; winter brings maple syrup season.

Spirits: Bear Swamp Orchard, a family-owned apple farm in Ashfield that produces hard cider and brandy.

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Where to eat in North County: We know you can work up an appetite while leaf-peeping. So here’s a quick eats cheat sheet:

Breakfast: The Break Room at Greylock Works in North Adams — Humble farm-sourced dishes (donuts, omelets) in a converted cotton-spinning factory.

Lunch: A-Ok Barbeque in North Adams — Berkshire BBQ served at a window and eaten at picnic tables.

Pub Grub: The '6 House Pub in Williamstown — Burgers and nachos in a converted 1896 barn.

Local Bites: Public Eat + Drink in North Adams — Local purveyors showcased in simple dishes like noodle bowls and Creole chicken.

Dog on the Go: Jack’s Hot Dog Stand in North Adams - An old-school counter that has been serving up dogs, burgers, and hand-cut fries since 1917.

Date Night: Mezze Bistro + Bar in Williamstown — Upscale farm-to-table dining overlooking three acres of rolling hills and a pond.

Dessert: Lickety Split in Williamstown and at MASS MoCA — 160 flavors of hand-crafted ice cream.

Where to drink in North County: Whether you’re craving caffeine or something a little stronger, we’ve got the solution:

Coffee Break: Brewhaha in North Adams — Fair-trade coffee, loose-leaf teas, and home-baked pumpkin-chip muffins in an early 1900s market with an art-deco façade.

Craft Brews: Bright Ideas Brewing in North Adams — Brewpub on the grounds at MASS MoCA. Order the Udderly Bright, made with sweet milk stout and chocolate malt.

Local Watering Hole: Old Forge in Lanesborough — An endless list of beers with a side of wings, please.

Artisanal Drinks: Berkshire Cider Project and The Distillery at Greylock Works in North Adams — You started the day at The Break Room (see breakfast above), now end it with hard sparkling cider made from forgotten apples or rum and gin crafted from botanicals foraged in the Berkshire Mountains.

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