As the Berkshires biggest city, Pittsfield can claim a rich history in agriculture, industry, literature, and baseball. But over the last century, as owners shuttered mills and General Electric relocated many of its manufacturing facilities, Pittsfield’s economic fortunes slid. Today, the city of about 44,000 is experiencing something of a renaissance, with a thriving arts and cultural scene and numerous opportunities to enjoy the natural beauty of the Berkshires.
The Whitehorse Inn (378 South St., 413-442-2512, www.whitehorsebb.com, rates $115-$250) is a beautifully maintained Colonial home next to the Housatonic River that offers delicious breakfasts with fresh fruit, homemade breads, and a convenient location near downtown cultural attractions. Hollyhock House (1130 Barker Road, 413-443-6901, www.hollyhockbb.com, rates $85-$150) offers three comfortable rooms, hardy breakfasts featuring homemade pastries and farm eggs, beautifully manicured gardens, and service with a smile from innkeeper Louise Filkins. Pittsfield has a handful of chain hotels available, but the Crowne Plaza Hotel Berkshires (1 West St., 413-499-2000, www.berkshirecrowne.com, rates $125-$285) is located in the heart of downtown and features an indoor pool and a full-service restaurant.
Visitors will find much to like from among a variety of offerings. The Misty Moonlight Diner (565 Dalton Ave., 413-499-2483, entrees $6.25-$14.99) serves breakfast all day in a ’50s-themed diner with a vintage Harley-Davidson on display and Elvis on the jukebox. If you’re looking for an epic eating challenge, tuck into the Godzilla, which includes a dozen eggs, home fries, and toast. It must be finished in a half-hour to win a T-shirt. On a Roll Cafe (75 North Street Suite 140, 413-236-5671, www.onarollcafeandcatering.com, sandwiches and salads $6.50-$10) has unusual and enticing offerings such as a barbecue chicken meatloaf sandwich and a pan-seared dill and cider salmon. Mazzeo’s (1015 South St., 413-448-2095, www.mazzeosristorante.com, entrees $17-$30) is a second-generation family-owned restaurant featuring Italian cuisine with homemade pasta, chicken, veal, and seafood. Flavours Restaurant (75 North St., entrance on McKay Street, 413-443-3188, www.flavoursintheberkshires.com, entrees $6.50-$20) offers authentic Malaysian cuisine in a casual atmosphere. One-of-a-kind dishes include steamed ginger and garlic baby clams in black bean sauce.
DURING THE DAY
Pittsfield has built a reputation as a regional hub for year-round cultural, creative, and outdoor pursuits. On the first Friday of every month, downtown retailers, businesses, and restaurants on North and South streets transform their spaces into art galleries for the First Fridays Artswalk (413-443-6501, www.firstfridaysartswalk.com, free admission). Visitors can meet local artists at over 20 locations and view their work. The Berkshire Museum (39 South St., 413-443-7171, www.berkshiremuseum.org, admission $6-$13) is a rare treasure because of its ability to connect with visitors by combining exhibits of art, history, and natural science in one museum. The museum will display the Festival of Trees through Jan. 2 with more than 100 holiday trees decorated to celebrate the nostalgia of the past, excitement of the present, and the possibilities of the future. The Lichtenstein Center for the Arts (28 Renne Ave., 413-499-9348, www.discoverpittsfield.com) hosts changing art shows with local artists in addition to classes, readings, and performances. Herman Melville’s Arrowhead home and museum may be closed during the winter, but the Melville Memorial Room at the Berkshire Athenaeum (1 Wendell Ave., 413-499-9480, ext. 204, www.pittsfieldlibrary.org/melville_room.html, free admission) contains an extensive collection of first-edition Melville works; paintings, prints, and autographs of the Melville family; and manuscripts, letters, and vintage volumes from Melville’s library. Cold, wintry weather only expands outdoor activity in Pittsfield because conveniently located Bousquet Mountain (101 Dan Fox Drive, 413-442-8316, www.bousquets.com, lift tickets $15-$45) offers over 20 trails of terrain for skiers of all ability levels. Hebert Arboretum (874 North St., 413-443-5348, www.hebertarboretum.org ) is a 231-acre haven for more than 50 species of trees and over 300 species of plants. The sanctuary of rolling hills, meadows, and streams is open all year and free to the public. Pittsfield State Forest (1041 Cascade St., 413-442-8992, www.mass.gov/eea/agencies/dcr/massparks) has over 30 miles of trails including the paved Tranquility Trail, and a stunning view of the Berkshires at the top of Berry Mountain. Canoe Meadows Wildlife Sanctuary (Holmes Road, 413-637-0320, www.massaudobon.org ) is a mere mile from the center of town with three miles of trails and a community garden along the Housatonic River. The Downtown Pittsfield group is promoting healthy exercise with the 2-mile Downtown Walking Loop (www.downtownpittsfield.com/downtown-loop ) that passes by the Colonial Theater, Park Square, and other downtown landmarks. Holiday shoppers should check out Persnickety Toys (137 North St., 413-236-8697), which features unique toys not found in big-box stores. Guido’s Fresh Marketplace (1020 South St., 413-442-9912, www.guidosfreshmarketplace.com) offers the freshest local produce, meats, and organic foods, in addition to wine tastings and nutritional seminars.
At the center of Pittsfield’s cultural renaissance is the Colonial Theater (111 South St., 413-997-4444, www.berkshiretheatregroup.org,) home to the Berkshire Theatre Group. Over $20 million was invested into restoring this historic theater where such legends as John Barrymore and Sarah Bernhardt once performed. Today more than a dozen different shows offer multiple performances throughout the year including “The Nutcracker’’ and “A Christmas Carol’’ in December. The highly regarded Barrington Stage Company (30 Union St., 413-236-8888, www.barringtonstageco.org ) begins its new season of performances in January. For live music, there are a number of fantastic options. The Underground Pub at the Crowne Plaza Hotel (see above) hosts local bands on Saturday nights. The Garage in the Colonial Theater showcases local acts in a range of genres. Missions Bar and Tapas (438 North St., www.missionbarandtapas.com) offers jazz on Mondays.