In the autumn, changing leaves form a dappled canopy of red and orange above the wavelike hills of the Berkshires. The summer crowds, who descended upon the region’s famed performing arts festivals, such as Tanglewood and Jacob’s Pillow, thin out. This majestic western Massachusetts landscape is thus prime for exploration.
Day 1
Consider starting your journey in the middle of scenic Berkshire County. Get into the spirit of the season at family-run Bartlett’s Apple Orchard. You can fuel up on coffee and cider doughnuts before picking your fill of up to 13 varieties of apple, such as McIntosh and Ida Red. Also on offer: raw honey, Massachusetts maple syrup and farm-fresh jams.
In nearby Pittsfield, Hancock Shaker Village is a restored settlement dating back to 1783. Families can watch blacksmithing demonstrations, attend a talk on Shaker life or hike the gentle Farm and Forest trail. Outdoor enthusiasts can drive to Pittsfield State Forest. About 30 miles of trails weave through the park, which crests along the Taconic Range.
Day 2
To the south, the historic town of Lenox is well worth a visit. Here you’ll find ornate cottages that look more like mansions. Some have been converted to inns and restaurants, while others are open for tours, including Ventfort Hall Mansion and Gilded Age Museum, once the residence of J.P. Morgan’s sister Sarah. Visitors can explore the first floor on their own or take a tour that lets them discover the second as well. The staff coaxes the past into the present through period events, such as teas and rounds of Bunco, a popular turn-of-the-century parlor game.
A 10-minute walk away, upcycled furniture is for sale at Second Home. Owner Suzannah Van Schaick and her husband, Pieter, search the area around Lenox for pieces to restore. Keep an eye out for silkscreen prints by local artists and vintage tableware, such as 1940s aluminum platters and midcentury tumblers. Nearby at MacKimmie Co., pillows covered in modern graphics (some designed exclusively for the store) are scattered among soft heirloom blankets and throws.
Enjoy the evening with dinner at Nudel, a small restaurant in the center of town that prepares dishes from local, seasonal ingredients in an open kitchen. Standouts include the roasted-purple-carrot tartare with Berleberg cheese, hazelnuts, Swiss chard and crumble fries.
Day 3
Brunch at Table Six is a leisurely way to start the day. Executive chef Ron Reda, who served for 4 years with the Clinton White House, devised a multicourse meal with champagne cocktails and mains such as brioche French toast or seared crab cake. If the weather is nice, opt for a table on the veranda with a view of the Berkshire Mountains.
In the afternoon visit Edith Wharton’s estate, The Mount. Wharton designed the country retreat based on principles she laid out in The Decoration of Houses (guides describe the estate as an autobiographical home). She wrote some of her most famous works here, including The House of Mirth and Ethan Frome. Don’t leave without strolling through the gardens, another of Wharton’s great passions.
Day 4
Meadows, wetlands and forests sweep down the slopes of Lenox Mountain at Pleasant Valley Wildlife Sanctuary. The varied paths offer options for all levels and are color coded to indicate whether a trail will take you farther out (blue dots) or back to the front desk (yellow dots). Keep an eye out for beavers on the Pike’s Pond Trail Loop; they typically come out at dusk.
Afterward discover Lee, one of many small towns typical of the region. When you’re hungry, 51 Park Restaurant & Tavern dishes out updated bar staples. Pizzas and strombolis are both made with house dough then cooked in a wood-fired oven. A short walk away, Moe’s Tavern pours American brews and more than 100 types of whiskey. Although it’s named for the bar on The Simpsons, don’t ask for a Duff equivalent: Owner Josh Cohen is serious about keeping only craft beers in his ever-rotating taps.
Day 5
You can get a healthy start at Starving Artists Café and Creperie, with its menu of vegetarian, vegan and gluten-free crêpes. The café seating spills over into Good Purpose Gallery. Gallery sales help support students attending the College Internship Program, which educates young adults on the autism spectrum or who have other learning differences.
The nearby town of Stockbridge was another favorite of 1800s cottagers. Naumkeag is a quintessential example of these country estates. Tours are required to see the house, so be sure to check for times in advance. The town is most well-known for the Norman Rockwell Museum, which houses the world’s largest collection of Rockwell’s work. The artist moved to Stockbridge in the 1950s, and his former studio has been moved onto the site.
Toast the day with a pint or two at Barrington Brewery & Restaurant, on the edge of Great Barrington. The brewpub uses energy from solar panels to produce an affordable selection of craft beers. Year-round pours include the Hopland Pale Ale and Barrington Brown Ale, while the Oktoberfest is a fall special.
Day 6
Great Barrington’s Main Street, about 10 miles south of Stockbridge, feels more modern than many of the Berkshires’ other towns. The Gypsy Joynt café gives off a hippie vibe thanks to walls plastered with eclectic posters, mismatched chandeliers and strings of multicolored lights. If you’re hungry, the fried Brussels sprouts and oven-baked-focaccia burgers are deeply satisfying. The Mr. Yunioshi burger, topped with homemade sriracha, grape salsa, goat cheese and avocado, is a mouthwatering blend of spicy and sweet.
Local painter Marilyn Kalish exhibits dreamy portraits across the street at Berkshire Vault Gallery, in a former bank. Part of the fun is stepping inside the namesake vault. Around the corner David Sedaris, Alan Cumming and Arlo Guthrie have walked the stage of the landmark Mahaiwe Performing Arts Center. Castle Street Café sits next door, making it a convenient spot to eat before a show. The seasonal menu is updated daily to reflect fresh ingredients brought in from local farms and producers. On Friday and Saturday night, jazz groups perform in the bar.
Day 7
Looking to pick up a few souvenirs on your last day in the area? Cadeaux sells vintage-style goods, such as hand-dyed ribbon and leather journals. At Farm and Home you can browse American-made furniture, ceramic dishes and waxed oilcloth totes. For foodies, Rubiner’s Cheesemongers & Grocers stocks small-batch spreads and vinegars as well as cheese and charcuterie. To sample some of their wares, head to the attached coffee shop, Rubi’s.
End your trip at Monument Mountain, a setting beloved by poets and painters for centuries. Nathaniel Hawthorne and Herman Melville first met on its slopes. At the summit, the boundaries of the Berkshires are visible, from the southern peaks of the namesake range to Mount Greylock on the county’s northern edge. You can map out your journey from start to finish and look down on the twisting rivers and amber hills that drew you and countless other travelers to this very spot.
THE DETAILS
Bartlett’s Apple Orchard: 575 Swamp Rd., Richmond; 413-698-2559; bartlettsorchard.com
Hancock Shaker Village: 1843 W. Housatonic St., Pittsfield; 413-443-0188; hancockshakervillage.org
Pittsfield State Forest: 1041 Cascade St., Pittsfield; 413-442-8992; mass.gov
Ventfort Hall Mansion and Gilded Age Museum: 104 Walker St., Lenox; 413-637-3206; gildedage.org
Second Home: 53 Church St., Lenox; 413-551-7050
MacKimmie Co.: 67 Church St., Lenox; 413-637-9060; mackimmieco.com
Nudel: 37 Church St., Lenox; 413-551-7183; nudelrestaurant.com
Table Six: Kemble Inn, 2 Kemble St., Lenox; 413-637-4113; tablesixlenox.com
The Mount: 2 Plunkett St., Lenox; 413-551-5111; edithwharton.org
Pleasant Valley Wildlife Sanctuary: 472 W. Mountain Rd., Lenox; massaudubon.org; 413-637-0320
51 Park Restaurant & Tavern: 51 Park St., Lee; 413-243-2153; 51parkrestaurant.com
Moe’s Tavern: 10 Railroad St., Lee; 413-243-6637; nocoorslight.com
Starving Artists Café and Creperie: 40 Main St., Suite 2, Lee; 413-394-5046; starvingartistcreperie.com
Good Purpose Gallery: 40 Main St., Suite 1, Lee; 413-394-5045; goodpurpose.org
Naumkeag: 5 Prospect Hill Rd., Stockbridge; 413-298-8138; thetrustees.org
Norman Rockwell Museum: 9 Glendale Rd., Rte. 183, Stockbridge; 413-298-4100; nrm.org;
Barrington Brewery & Restaurant: 420 Stockbridge Rd.; 413-528-8282; barringtonbrewery.net
Gypsy Joynt Café: 293 Main St., Great Barrington; 413-644-8811; gypsyjoynt.com
Berkshire Vault Gallery: 322 Main St., Great Barrington; 413-854-7744; berkshirevaultgallery.com
Mahaiwe Performing Arts Center: 14 Castle St., Great Barrington; 413-528-0100; mahaiwe.org
Castle Street Café: 10 Castle St., Great Barrington; 413-528-5244; castlestreetcafe.com
Cadeaux: 274 Main St., Suite 2, Great Barrington; 413-528-1972; cadeauxgb.com
Farm and Home: 276 Main St., Great Barrington; 413-528-9100; farmandhome.us
Rubiner’s Cheesemongers & Grocers: 264 Main St., Great Barrington; 413-528-0488; rubiners.com
Rubi’s: 256 Main St., Great Barrington; 413-528-0488; rubiners.com
Monument Mountain: Rte. 7, Great Barrington; 413-298-3239; thetrustees.org
NOTE: Information may have changed since publication. Please confirm key details before planning your trip.