Feature: Berkshires Day by Day

Gilded Age mansions, golden hills and byways lined with white pines draw travelers to this artsy Massachusetts enclave.

By Jessen O’Brien

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: Visitors can pass through the stately halls of the summer retreats of Gilded Age industrialists or climb the surging peaks that inspired some of that era’s most famous writers, such as Herman Melville and Edith Wharton. These sites are linked by roads that are not just a means but also a pleasure: well-paved lanes that cut crescents through thickets of skinny trees, that rise and dip, giving the illusion of an ever-shifting horizon, that afford Thoreauvian vistas. Farm-to-table restaurants, a year-round arts scene and shops brimming with handcrafted goods round out the area’s timeless appeal.

Day 1

Consider starting your journey in the middle of scenic Berkshire County (berkshires.org). Get into the spirit of the season at family-run Bartlett’s Apple Orchard (575 Swamp Rd., Richmond; 413-698-2559; bartlettsorchard.com; a half bushel, $18). 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 (1843 W. Housatonic St., Pittsfield; 413-443-0188; hancockshakervillage.org; adults, $20) 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 (1041 Cascade St., Pittsfield; 413-442-8992; mass.gov; parking, $6 a car for out-of-state vehicles). 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 (104 Walker St., Lenox; 413-637-3206; gildedage.org; adults, $18), 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 (53 Church St., Lenox; 413-551-7050). 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. (67 Church St., Lenox; 413-637-9060; mackimmieco.com), 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 (37 Church St., Lenox; 413-551-7183; nudelrestaurant.com; dinner for two, $80*), 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 (Kemble Inn, 2 Kemble St., Lenox; 413-637-4113; tablesixlenox.com; Sunday brunch for two, $70) is a leisurely way to start the day. Executive chef Ron Reda, who served for four 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 (2 Plunkett St., Lenox; 413-551-5111; edithwharton.org; adults, $18). 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. In a letter, she wrote about them: “…[T]his place, every line of which is my own work, far surpasses The House of Mirth.”

Day 4

Meadows, wetlands and forests sweep down the slopes of Lenox Mountain at Pleasant Valley Wildlife Sanctuary (472 W. Mountain Rd., Lenox; massaudubon.org; 413-637-0320; adults, $5). 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 (51 Park St., Lee; 413-243-2153; 51parkrestaurant.com; dinner for two, $40) 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 (10 Railroad St., Lee; 413-243-6637; nocoorslight.com; drinks for two, $20) 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 (40 Main St., Suite 2, Lee; 413-394-5046; starvingartistcreperie.com; breakfast for two, $30), with its menu of vegetarian, vegan and gluten-free crêpes. The café seating spills over into Good Purpose Gallery (40 Main St., Suite 1, Lee; 413-394-5045; goodpurpose.org). 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 (5 Prospect Hill Rd., Stockbridge; 413-298-8138; thetrustees.org; adults, $15) 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 (9 Glendale Rd., Rte. 183, Stockbridge; 413-298-4100; nrm.org; adults, $18), 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 (420 Stockbridge Rd.; 413-528-8282; barringtonbrewery.net; drinks for two, $12). 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 (293 Main St., Great Barrington; 413-644-8811; gypsyjoynt.com; lunch for two, $30) 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 (322 Main St., Great Barrington; 413-854-7744; berkshirevaultgallery.com), 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 (14 Castle St., Great Barrington; 413-528-0100; mahaiwe.org; ticket prices vary). Castle Street Café (10 Castle St., Great Barrington; 413-528-5244; castlestreetcafe.com; dinner for two, $60) 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 (274 Main St., Suite 2, Great Barrington; 413-528-1972; cadeauxgb.com) sells vintage-style goods, such as hand-dyed ribbon and leather journals. At Farm and Home (276 Main St., Great Barrington; 413-528-9100; farmandhome.us) you can browse American-made furniture, ceramic dishes and waxed oilcloth totes. For foodies, Rubiner’s Cheesemongers & Grocers (264 Main St., Great Barrington; 413-528-0488; rubiners.com) 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 (256 Main St., Great Barrington; 413-528-0488; rubiners.com).

End your trip at Monument Mountain (Rte. 7, Great Barrington; 413-298-3239; thetrustees.org; parking, $5 a car), 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.

RCI® affiliated resorts in the Berkshires include:
Holiday Inn Club Vacations Oak ’n Spruce Resort 1243

Kids delight in the on-site playground and miniature-golf course. 190 Meadow St., South Lee
Member Review: “Close to many dining options.”

Wind in the Pines 1903

Access to outdoor activities, shopping and great restaurants make this an idyllic Berkshire getaway. 949 S. Main St., Great Barrington
Member Review: “Quiet, peaceful setting.”

Vacation Village in the Berkshires 6057

All of the cozy accommodations feature a kitchen and a hot tub. 276 Brodie Mountain Rd., Hancock
Member Review: “Spacious rooms and attentive staff.”

Berkshire Mountain Lodge D567

When you’re not out and about, you’ll appreciate the resort’s modern amenities and plush living and dining areas. 8 Dan Fox Dr., Pittsfield
Member Review: “Quiet, beautiful grounds and nice facilities.”

For complete member reviews (as member reviews have been condensed) and additional resort listings, visit RCI.com or call 800-338-7777 (Weeks) or 877-968-7476 (Points). Club Members, please call your specific Club or RCI telephone number.

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Non-affiliated RCI Resorts:
Federal House Inn

An elegantly restored 1820s home, converted into a stately bed-and-breakfast. Guests can mingle during a daily wine and cheese hour or relax in one of the Adirondack rocking chairs set on the front porch. 1560 Pleasant St., Rte. 102, South Lee; 413-243-1824; federalhouseinn.com; doubles from $185 a night

Gateways Inn & Restaurant

Norman Rockwell used to regularly dine at this inn, formerly Harley Procter’s summer cottage. The bar stocks more than 200 types of whiskey, and on weekends you can enjoy live music along with your drink. 51 Walker St., Lenox; 413-637-2532; gatewaysinn.com; doubles from $180 a night

  • *Estimated meal prices do not include drinks, tax, or tip.
  • *All prices are in USD.
  • NOTE: Information may have changed since publication. Please confirm key details before planning your trip.
  • Published: Fall 2016