Berkshires Attractions & Things to Do on Vacation in Lenox, MA


Summer home of the Boston Symphony Orchestra

Access to Tanglewood from the Apple Tree Inn

The Apple Tree Inn is located across the road and up the hill from Tanglewood. It is about a 15-minute walk or a 5-minute drive to Tanglewood. We recommend walking, if possible, because traffic leaving a well-attended concert can be very heavy with lengthy delays. The inn is up a steep hill from Tanglewood, so you do need to be able to complete a steep uphill walk on the return trip. 

Tickets to Concerts at Tanglewood

We can purchase tickets prior to when they go on sale to the general public and would be happy to get tickets for guests. There is a $5 processing fee per ticket, we are usually able to get very good seats.

Pre Concert Dining

There are many fine restaurants in Lenox; however, we recommend a very early dinner on the night of well-attended concerts, dining at Tanglewood, or purchasing a picnic from one of the recommend vendors listed  below to avoid getting stuck in heavy traffic returning from Lenox to Tanglewood. If you purchase a picnic, you can consume it on our deck or by our pool, or on the grounds at Tanglewood.


Nejaimes Wine Cellar – Nejaimes is a well-stocked wine and liquor store, which also sells high-end cheese and food prepared in-house. You can order prepared picnics in advance or purchase packaged food items in the store.

Loeb’s Foodtown – Loeb’s is an old-fashioned grocery store with an excellent deli. Made-to-Order sandwiches and deli salads, chips, bread, fruit, beverages.

Guido’s Fresh Marketplace – Guido’s is a well-stocked gourmet market, which offers a wide variety of fresh and prepared foods, cheese and wine.

Dining at Tanglewood

Tanglewood Café and Grill

The Tanglewood Café and Tanglewood Grill offer a casual dining experience for all patrons. Stop in and take advantage of the fresh salad bar, sandwiches made to order, hot foods, and a wide variety of beverages for your enjoyment on the lawn or under the covered seating areas. The Café is located between the Shed and the Lion’s Gate. The Grille is located just inside the Main Gate next to the Glass House Gift Shop. 

The Grill and Cafe is not open for performances in Ozawa Hall. Limited snack options are available at the Ozawa Hall concession stand.


During the season, have more time to enjoy Tanglewood by ordering a picnic in advance and dining on the grounds from Tanglewood. 


For light snacks and beverages, the shed, and Tappan Shacks, and the shed Beer Garden will open when the grounds open for Shed concerts. The Bernstein Gate Concession opens when the grounds open for Ozawa Hall.

Highwood Manor House Dining

The Highwood Manor House will be open to the public for dinner Friday and Saturday, and Sunday brunch. Highwood offers an elegant buffet dinner at a fixed price of $65 per person and a Sunday Brunch buffet for $45 (inclusive of tax; 18% gratuity will be added to the bill). Cocktails, bottled wine, and á la carte desserts are also available. For reservations, call 413-637-4486 at least 48 hours in advance, reservations are required. Highwood will also be open post-concert on Sundays for cocktails and light appetizers for Boston Symphony concerts only.

Kripalu Center for Yoga and Health

Kripalu, the world-renowned yoga and health center, is located just down the hill from the Apple Tree Inn.  It is about a 15-minute walk or a 3-minute drive. Many of our guests stay with us while taking programs at Kripalu.

We offer a 10% discount on stays of 2 – 4 nights, when our guests are registered for a program at Kripalu, and a 20% discount on stays of 5 nights or more.  The stay must be booked directly with the Apple Tree, either by phone or on our website to qualify for the discount.


Arrowhead, home of Herman Melville

18th-century farmhouse where Melville wrote Moby Dick. National Historic Landmark. Guided tours, historic farm project, museum shop. 

Berkshire Botanical Garden

One of America’s oldest botanical gardens featuring 23 seasonal display gardens, classes, and special exhibits. Open daily year round.

Berkshire Museum

Art, history & natural science. Aquarium, fine art, Curiosity Incubator, programs & activities for all ages, Museum Shop. M-Sat 10-5pm; Sun 12-5pm.

39 South Street, Pittsfield MA 01201 – (413) 443-7171

Berkshire Scenic Railway Museum

Restored 1903 Lenox Station museum with interactive railroad exhibits and gift shop. Open weekends and holidays, 9am – 4pm, June – October.

10 Willow Creek Road, Lenox MA 01240 – (413) 637-2210


Summer home, studio & gardens of Daniel Chester French, the Lincoln Memorial Sculptor. Outdoor contemporary sculpture/special programs. Kids under 13 free.

Clark Art Institute

Enjoy exceptional art and architecture in an unparalleled setting. European, American, British, Old Master paintings, walking trails, café and gift shop.

Crane Museum of Papermaking

Exhibition papermaking through more than two centuries of the oldest paper company in America. Free Admission.  June – Oct, M-F; Nov – May, Tue – Thurs; 1 – 5pm.

Frelinghuysen Morris House & Studio

Bauhaus-inspired home/studio displaying Cubist Masters +original furnishings 46-acreestate/Guided Tours/Workshops. Late June-Columbus Day.

Hancock Shaker Village

Utopia, closer than you think. Demonstrations, heritage breed animals, gardens, & trails. Seed Market Cafe & Shaker Mercantile. Kids 12 & under FREE.

Mass MoCa

Open year-round and housed in a restored 19th-century factory, they are the country’s largest center for contemporary visual and performing arts.

Naumkeag House & Gardens

Gilded Age mansion with original furnishings and art. Ten acres of iconic gardens designed by Fletcher Steele. Open April – December.

Norman Rockwell Museum

A MUST SEE! Norman Rockwell’s original paintings, his studio (open seasonally), changing American Illustration exhibitions. Museum open year-round.

The Mount, Edith Wharton’s Home

Experience the beauty of Edith Wharton’s historic estate and gardens. Admission includes guided tour. Gift shop, outdoor dining and special events. Open May – February.

Ventfort Hall Mansion and Gilded Age Museum

Open year round. Built in 1893 by JP Morgan’s sister, Sarah. Tours/tea & talks/concerts/lectures/weddings/private rentals. Cider House Rules film set. 

Williams College Museum of Art

WCMA sparks new ways of thinking about the visual world through its innovative exhibitions, programs, publications and initiatives.

Barrington Stage Company

Award-winning professional theatre presenting top-notch musicals, masterful classics, thought-provoking new work, cabarets and youth theatre. May-Oct & Feb. 

Berkshire Opera Festival

Berkshire Opera Festival presents live opera and recital performances to the Berkshire region during an annual summer festival. 

Berkshire Theatre Group

The Colonial Theatre & Berkshire Theatre Festival present theatre, live music, comedy, family programming and more year round!

Jacob’s Pillow Dance Festival

International dance festival and Nat’l Historic Landmark; 300+ free and ticketed performances, talks, exhibits, tours & onsite dining. June-August.

Shakespeare & Company

One of the largest and most esteemed destination theatres in the country, offering a vibrant performance season in repertory from May – November.


Idyllic summer home of the Boston Symphony Orchestra. Enjoy classical, jazz, popular music, a wine & food festival & more, late June – Labor Day weekend. 

Williamstown Theatre Festival

Tony Award-winning theatre offers performances each summer featuring the finest American actors. Tues.-Sat. evening; Thurs., Sat., Sun. matinee.


A small area with world-class food, the Berkshires offers great eateries that always stand out as wonderful memories. The following is only a sample of the wonderful dining available in Lenox and other parts of the Berkshires.

Alta Wine Bar & Restaurant – Unique casual wine bar/restaurant. 20+ wines by the glass. Fresh local ingredients. Outdoor dining. Full bar/lunch/dinner 7 days. Owner operated.

Blantyre – Fine dining-elegant setting-piano music. Wine Spectator Grand Award – Relais & Chateau. Open year round. Resort casual.

Brava – Come in for our wide selection of wine by the glass, beer on tap, tapas, pizzas, cheese and charcuterie. They do not take reservations. Seating is first come, first served. Open daily from 5pm-1am. The kitchen serves food until midnight.

Café Lucia – Featuring regional Italian preparations, local organic produce, natural & organic meats, fresh fish & seafood. Excellent wines, full bar. Fine dining in former 1840’s farmhouse. Chef owned and operated since 1983. Air-conditioned or alfresco dining on covered Mahogany deck amid flower gardens. Private parties welcome, take-out available. Reservations appreciated.

Chez Nous – Fine cuisine in a casual, warm atmosphere. Their focus is always on quality & consistency and their “half portion options” give guests even more healthy and delicious choices.

Chocolate Springs Café – European-style chocolates & desserts. One of Top 10 chocolatiers in US by Saveur Magazine. Enjoy classic truffles, pralines, unique tea infusions, our own ice cream & sorbet, mousse cakes, pastries. Serious 
hot/cold chocolate, teas & coffees. Open daily.

Church Street Cafe – American bistro under new management, creative menus for lunch/dinner. Fresh local ingredients, extensive wine list, al fresco dining. Owner operated.

Cranwell – Wyndhurst, Music Room & Sloane’s Tavern. Fine dining in historic hilltop Mansion. Casual indoor/outdoor at Sloane’s. Spa menu items. Open daily. Wine Spectator Award. Zagat rated.

Elizabeth’s – When a restaurantthis small in an out-of-the-way part of town has made it this long and is a hands-downlocal favorite, you know they are doing something right. Longtime low-key Italian institution with an open kitchen.  You can sit on the first floor and watch dinner being prepared.  Delicious, fresh pasta, big shared salads with seasonal ingredients and some meat dishes. Everything is made on the premises.

Firefly Gastropub – Vibrant, chef-owned Church St. landmark. Ever-changing menus featuring local, farm-sourced ingredients. Beautiful dining rooms.  Eat. Drink. Laugh!

Frankie’s Café Italiano – Traditional Italian food at its best. Fresh, local ingredients. Outdoor dining, full bar, extensive wine list. Cozy & romantic atmosphere. A/C. Dishes “like our Mama use to make.” Open 7 days for dinner at 5:00pm

Gateways Inn & Restaurant – The restaurant offers a farm-to-table menu of creative and contemporary American dishes. The philosophy of the culinary team is to utilize the finest and freshest local products available, and their seasonal menus reflect this goal.  Join in the lounge for a lighter fare with live music at 7:30pm. Featuring the finest whiskey collection in the Berkshires! Hours are Fridays and Saturdays from 5pm – late. Open 7 nights a week in July and August.

Haven Café  & Bakery – Handcrafted, ingredient-driven food. Artisanal-style bakery, espresso drinks, wine & beer. Take-away, picnics, catered private events. Seasonal outdoor seating. Breakfast & lunch daily. Call for evening hours. 8 Franklin Street, Lenox, MA 01240

Olde Heritage Tavern – “Lenox, Plain & Simple.” Great food, great people, great fun. Private parties & catering available. Serving over 42 beers. Come with friends or the whole family. Now serving breakfast. It’s the local hangout!

Prime Italian Steakhouse & Bar – Featuring prime cuts w/an array of Italian specialties. Striking glass bar, magnificent wine list, late-night menu after Tanglewood, patio dining, A/C, enclosed semi-private glass booths. Open year-round. Reservations suggested.

Table Six Restaurant – Expertly prepared seasonal cuisine, first-class service and casually elegant historic setting. Seasonally; best outdoor dining.

The Scoop – A vibrant sweets café serving Blondie’s homemade ice cream made onsite daily. The Scoop also offers frozen yogurt, smoothies, candy, fresh-baked goods, No. 6 Depot coffee, and much more. Open 7 days a week May – September. Stop in for some sweetness with the friendliest staff in town and enjoy some of Blondie’s famous flavors on our porch, great for people watching. Customized ice cream cakes and hand-packed pints/quarts are also available upon request. Life is short – eat dessert first.

Trattoria Il Vesuvio – A taste of Italy in the Berkshires. Come for the atmosphere, stay for the food. Fine Italian cuisine. Weekly specials. Open daily. Reservations suggested.

Wheatleigh – Sophisticated country house hotel with the only 5-Diamond Restaurant in Western MA. Glass-enclosed portico available for private events. Casual dining in The Library. Open year-round. Lunch & dinner served daily, Sunday Brunch.

Shopping in the Berkshires

The shopping is one of the many attractive features of the Berkshires. From historic Lenox south to Stockbridge and West Stockbridge, Great Barrington and the outlets in Lee and north to Pittsfield there are wonderful, unique shops.  You can buy clothing, pottery, art glass, chocolate, wine, art, books, yarn, leather, mobiles, extracts, jewelry, shoes, home goods, anything and everything! Check it out!