The Bear: The Bear Cafe was created in 1971 by Albert Grossman, the former music industry mogul who led Bearsville Records and Studios and managed Bob Dylan, The Band, Todd Rundgren, Janis Joplin and Peter, Paul & Mary, among others. Grossman personally designed and financed the Bearsville Theater Complex, which features The Bear Cafe, The Little Bear, Bearsville Theater, and the former Utopia Video Complex, now home to WDST Radio. The Bear is a Woodstock classic. Peter Cantine and Chef Eric Mann have run The Bear since 1988 and, along with another investor, bought the entire complex in 2004 from Sally Grossman, Albert’s widow. The Bear’s decor features hardwood floors, a grand fireplace and signature oil paintings by local Woodstock artist Jo Cantine, Peter’s late aunt. The cafe closed in 2018 and the building is currently under renovation.
Contact info: The Bear Cafe, Route 212, Bearsville, NY 12409; (845) 679-5555; http://www.bearcafe.com
Black Bear Restaurant, Tavern and Lodge: Black Bear features a casual dining experience. Open for breakfast, lunch and dinner. Black Bear closed in July 2009.
Contact info: Black Bear Restaurant, Tavern and Lodge, 1802 State Road 28, Woodstock, NY 12498; (845) 657-7133; http://www.blackbearwoodstock.com
Blue Mountain Bistro Catering: Blue Mountain Bistro Catering is located on Route 28 in Kingston at Bistro-To-Go and has been serving the Woodstock area since 1993, when the original restaurant opened in town. Owners Richard and Mary Anne Erickson closed the restaurant portion of their business in 2005 to focus strictly on catering. They specialize in Mediterranean-inspired food and offer extensive catering services, as well as fully prepared “take-home” meals. Blue Mountain is open 7 days a week: 9 a.m. to 7 p.m. Monday-Thursday, 9 a.m. to 8:30 p.m. Friday, and 11 a.m. to 5 p.m. Saturday and Sunday.
Contact info: Blue Mountain Bistro Catering / Bistro-To-Go, 948 Route 28, Kingston, NY 12401; (845) 340-9800; http://www.bluemountainbistro.com
Bread Alone Bakery and Cafe: Bread Alone is a European-style bakery, using only organic flours and grains. Visitors can learn more about Bread Alone’s baking process by taking a tour of their main store in Boiceville, NY.
Contact info: Bread Alone Bakery and Cafe, 22 Mill Hill Road, Woodstock, NY 12498; (845) 679-2108; http://www.breadalone.com
Catskill Rose, Mount Tremper: Catskill Rose opened in 1987 and offers a high-end Continental menu with a full bar and wine list. All foods are made from scratch in house and daily specials are offered.
Contact info: Catskill Rose, 5355 Route 212, Mount Tremper, NY 12457; (845) 688-7100; www.catskillrose.com
Cucina: Cucina is situated in an old farmhouse at the intersection of Route 375 and Route 212 and boasts a “contemporary Italian menu.” The restaurant offers several ways to dine: there’s a 24-seat communal table in one room, a smaller private room, or eat outside on the extra-wide front porch. Cucina is open 7 nights a week from 5-11 p.m. and serves brunch on Saturday and Sunday from 11 a.m. to 5 p.m.
Contact info: Cucina, 109 Mill Hill Road, Woodstock, NY 12498; (845) 679-9800; http://www.cucinawoodstock.com
Garden Cafe on the Green: Woodstock’s Garden Cafe on the Green is a vegetarian restaurant which offers a menu prepared with “fresh, organic and high quality ingredients.” The cafe serves breakfast, lunch and dinner.
Contact info: Garden Cafe on the Green, 6 Old Forge Road, Woodstock, NY 12498; (845) 679-3600; http://woodstockgardencafe.com
Joshua’s Cafe and Caterers: Joshua’s, another mainstay Woodstock eatery, features a diverse menu from Middle Eastern to Eastern European cuisine. The restaurant is located in the heart of town. Live local musicians and poetry readings can often be found in the upstairs bar on weekends. Joshua’s is open for breakfast, lunch and dinner and offers catering services.
Contact info: Joshua’s Cafe, 51 Tinker Street, Woodstock, NY 12498; (845) 679-5533; http://www.joshuascafe.com
Landau Grill: Landau Grill, situated in the middle of town, is a warm, comfortable gathering spot for both townspeople and visitors. The former Woodstock Pub is now a quaint room that offers a quality assortment of American food. Table-dining is available inside, or at the large bar for a cozier experience. Seating is also available outside. Closed in 2018.
Contact info: Landau Grill, 17 Mill Hill Road, Woodstock NY 12498;
The Little Bear: Located at the edge of Woodstock in the Bearsville Theater Complex, The Little Bear is recognized as one of the finest Chinese food eateries in the Hudson Valley. The complex was created in 1971 by Albert Grossman, music industry mogul. The Little Bear, like all Woodstock eateries, features a casual dining experience and offers an array of meal choices, including an extensive vegetarian menu.
Contact info: The Little Bear, Route 212, Bearsville, NY 12409; (845) 679-8899; http://www.bearsystems.com/lilbear/lilbear.html
Maria’s Bazaar: Maria’s, a family-owned business, is open daily from 7 a.m. to 8 p.m. for breakfast, lunch and dinner. It features Northern Italian foods, such as homemade soups and pasta dishes. Eat on the private patio or visit the deli and bakery for an on-the-go meal.
Contact info: Maria’s Bazaar, 21 Mill Hill Road, Woodstock, NY 12498; (845) 679-5434
Mountain Gate Indian Restaurant: Mountain Gate is an authentic Indian cuisine restaurant, offering an array of dishes. The restaurant is open 6 days a week for lunch and dinner with a buffet on Tuesday. It is closed on Monday.
Contact info: Mountain Gate Indian Restaurant, 4 Deming Street, Woodstock, NY 12498; (845) 679-5100
New World Home Cooking, Saugerties: New World’s Chef Ric Orlando offers fusion cooking, with a distinctive taste and a spicy kick. There’s an array of choices for spice levels and special dietary accommodations are available. Lunch and dinner are served every day. Reservations are recommended. New World features live music every Friday night. Closed in 2018.
Contact info: New World Home Cooking, 1411 Rt. 212, Woodstock/Saugerties, NY; (845) 246-0900; http://www.newworldhomecooking.com
Oriole 9 Cafe:Oriole 9 boasts “flavors of the Mediterranean.” They open daily at 8:30 a.m. for breakfast; lunch is served until 5 p.m. Dinner is served from 5-11 p.m. Catering services also are available.
Contact info: Heaven, 17 Tinker Street, Woodstock, NY 12498; (845) OR9-5763; http://www.oriole9.com
Red Onion Restaurant & Bar: The Red Onion is located on Route 212 at the end of Woodstock. This international bistro offers casual dining and features a wide variety of entrees and daily specials. Ice creams and desserts are made on the premises. It opens daily at 5 p.m. for dinner and is closed on Wednesday.
Contact info: Red Onion Restaurant & Bar, 1654 Route 212 at Glasco Turnpike, Woodstock, NY 12477; (845) 679-1223; http://www.redonionrestaurant.com
Reservoir Inn, West Hurley: The Reservoir Inn is open for lunch and dinner, and offers party, meeting and catering services as well. The menu features weekly, daily and early-bird specials. Hours are Monday, Tuesday and Wednesday from 5-9 p.m. for dinner; Thursday and Friday from 11:30 a.m. to 2 p.m. for lunch, 5-9 p.m. for dinner on Thursday, 5-10 p.m. for dinner on Friday; Saturday from 12-3 p.m. for lunch, 5-10 p.m. for dinner; Sunday from 1-9 p.m. for dinner.
Contact info: Reservoir Inn, 167 Basin Road, West Hurley, NY 12491; (845) 331-9806; http://www.reservoirinn.biz
Taco Juan’s: Taco Juan’s features Mexican food and an ice cream bar. It’s located across from the Green in the center of town and offers eat-in and take-out accommodations.
Contact info: Taco Juan’s, 31 Tinker Street, Woodstock, NY 12498; (845) 679-9673
Tin Pan Alley, Red Hook: Tin Pan Alley is open seven days a week for dinner, with both indoor and outdoor dining available, weather permitting. Order from their extensive dinner menu, or from a lighter fare bar menu. The restaurant offers daily soup, wine and desert specials. Weekly specials include Wing Night, featuring nine different flavors of wings, Prime Rib night and an extensive Sunday Brunch.
Contact info: Tin Pan Alley, 7909 Old Post Road (Route 9), Upper Red Hook, NY 12571; (845) 758-4545; http://www.tinpanalleyrestaurant.com/redhook
Traphagen Restaurant, Rhinebeck: The Traphagen is located at the historical Beekman Arms in Rhinebeck. The colonial-style Arms was built in 1766. It is listed in the National Register of Historic Places and is referred to as “America’s oldest Inn.” Dining at the Traphagen Restaurant is available in one of several dining rooms or in the garden greenhouse. Lunch and dinner is served year round, as well as Sunday brunch. The menu is seasonal and vegetarian requests can be accommodated.
Contact info: The Beekman Arms and Delamater Inn, Route 9, Rhinebeck, NY 12572; (845) 876-7077; http://beekmandelamaterinn.com/restaurant.htm
Wok ‘n Roll Cafe: The Wok ‘n Roll offers Japanese food in one dining room; Chinese food is offered in yet another. Special dietary and/or health dishes are available on request. Closed in 2019
Contact info: Wok ‘n Roll Cafe, 50 Mill Hill Road, Woodstock, NY 12498; (845) 679-7760
Yum Yum Noodle Bar: Neighboring the Woodstock Music Shop, Yum Yum Noodle Bar offers Asian style cuisine including noodle bowls, salads, sides and appetizers.
Contact info: Yum Yum Noodles, 4 Rock City Road, Woodstock, NY 12498 (845) 679-7992; http://www.yumyumnoodlebar.com