Where to: Woodstock area



Overlook Trail and KTD Monastery

The legend has it that if you spend three nights (or one night — legends tend to conflict) in the shadow of Overlook Mountain, you will always return to Woodstock (or, in an alternate version, you will never leave.)

However it is, those who have stayed, or left and come back, may swear by it, and all can tell you of their experience climbing Overlook. Actually it’s more of a hike, though a distinctively uphill hike of 2.5 miles to the summit of Overlook, a magical place where you’ll find one of the Catskill Mountains’ finest restored Fire Towers. Ascend to the top of the tower and you’ll find one of the most majestic views of the town, the Ashokan Reservoir and the Hudson Valley, and indeed you’ll find yourself pulled into the magic that Woodstock exerts. You’ll have passed the ruins of the old Overlook Mountain House, which in the early 1900s was the fashionable stop for the summer folks. To get to the trailhead, you turn right at the Village Green, go up Rock City Road, then straight up Meads Mountain Road until you reach the trail at the top, just across from KTD Monastery, the North American seat of Tibetan Buddhism, and an attraction all of its own.

The Monastery, which has been visited by The Dalai Lama offers Dharma teachings and practice retreats in the Karma Kagyu tradition of Tibetan Buddhism. The Main Shrine Room is open 2 p.m.-6 p.m. Monday-Friday, and, if a teaching not occurring, 10 a.m.-noon and 1 p.m.-6 p.m. Saturday and Sunday. Free guided tours are available to the general public at 1 p.m. on Saturdays and Sundays. You can phone before coming to be sure that the tour will occur, 845-679-5906, extension 3. For more information, see https://www.kagyu.org



Woodstock Playhouse

The Woodstock Playhouse was first built in the early 1900s, then destroyed by fire in the 1930s. It was rebuilt in 1937, the barnlike structure becoming a hub for theater and performance in Summer Stock and for concerts. Through the 1960s it maintained its reputation for first class offerings, with theatrical stars treading the boards and crowds of residents and summer visitors jamming the seats.

By the 1980s summer theater at the Playhouse had reached its nadir, and in 1987 a giant fire destroyed every last stick of it.

The town of Woodstock created a gateway overlay to its zoning regulations to protect the property from the suburban strip mall style development, and the local citizenry banded together in a Quixotic quest to restore the property to its former glory. Against all odds, dollars mounted up, one by one, and the property was purchased, a small bandshell erected and performance was once again present. A dedicated group, The Woodstock Arts Board, raised more funds and constructed an indoor/outdoor theater and ran productions. But just as they ran out of steam, the playhouse was purchased by the professionals who run the New York Conservatory for the Arts. The structure was again renovated and enclosed with all new seats, equipment and layout, and now features a range of programs from large summer productions to classical music, to smaller show, and has resurrected the long tradition of the property. You can find out more by going to www.WoodstockPlayhouse.org or by calling 845-679-6900. It is located at the entrance to Woodstock, 103 Mill Hill Road.


Upstate Films

The Rhinebeck-based Upstate Films expanded into Woodstock more than two years ago with its eclectic mix of independent and small studio films that appeal to a wide variety of audiences. The venue is the venerable Tinker Street Cinema, once the Woodstock Methodist Church that became a theater in 1967, now rechristened as Upstate Films and it is a non-profit operation programming the screenings.

In business now for 30 years, Upstate believes in film “as a medium of social communication and aesthetic experience. Its programming (700+ screenings per year) is an eclectic mix which, in the course of any particular year, focuses on themes, issues, regions.” You can see movies that are rarely shown in this country, older films, from the profound to the comedic (and often both) that you won’t find at commercial venues.

Upstate Films is at 132 Tinker Street, Woodstock. Call 845-679-6608 for times and information or see upstatefilms.org.


Bearsville Theater

Albert Grossman, who managed Bob Dylan, Peter Paul and Mary, and Janis Joplin, built the Bearsville Theater in the late 1970s, to be a premier music and performance space, with quality sound and sightlines. When Grossman died in 1986 the theater had not been used, and it wasn’t until the dawn of the 21st Century that it got rolling. But it has proven to be a high class small concert space that hosts artists such as Steve Earle, The California Guitar Trio, Richard Thompson, The Texas Playboys, Jack DeJohnette, the Farewell Drifters and is an important stop along the way for artists who usually play much larger spaces, but want to perform in Woodstock. It’s also the home to events such as the Woodstock Invitational Luthier’s Show in October, The Woodstock Writer’s Festival in April, and is a major participant in the Woodstock Film Festival in September. The theater sits on the property that also houses world class restaurants, The Bear Café and the Little Bear.

The theater itself seats 250 comfortably, but through a huge glass wall from the bar and lounge area you can also see the show, as the fine sound system projects the formal performance into a less formal atmosphere.

The Bearsville Theater is at 291 Tinker St., Woodstock. Call 845-679-4406 for more information, or see bearsvilletheater.com


Bluegrass Clubhouse

Every Thursday for more than seven years now, the Bluegrass Clubhouse convenes at the Harmony Café at the Wok ‘n Roll restaurant, 52 Mill Hill Road. This sort of hidden-in-plain-sight event features The Saturday Night Bluegrass Band (even though it plays on Thursdays) with the incredible banjo legend Bill Keith (who played with Bill Monroe and the Bluegrass Boys back in the day), along with Brian Hollander on guitar and vocals; Tim Kapeluck on mandolin and vocals; Guy ‘Fooch’ Fischetti on fiddle and pedal steel guitar; and Geoff Harden on bass and vocals. Their special guests run from the obscure to some of the finest musicians the town of Woodstock has to offer coming by to sit in for a song or two. All it will ever cost you is a donation into the jar and you get two sets of fine acoustic Americana music, and it keeps happening when the week turns to Thursday. Also available is fine Chinese and Japanese food. Call Harmony Café, where there is a musical event seven nights per week, at 845-679-7760.


WAAM, Guild, and galleries

In a community that is well known for its artists, the places to show that artwork take on paramount importance, and here they are world class.

The Woodstock Artists Association and Museum, at 28 Tinker Street in the heart of town, houses several galleries and an adventurous lineup of shows featuring artists who are members, and outside curators who will come in and add perspective to the features. The Phoebe Towbin Wing gallery most often shows artwork from Woodstock artists whose work has been selected in the Museum’s own collection, ranging from George Bellows, Yasuo Kuniyoshi, Karl Fortess, Konrad Cramer and others from the art scene’s halcyon days in town.

Right next door, at 34 Tinker Street, is the Woodstock-Byrdcliffe Guild’s Kleinert/James Arts Center, which, in addition to showing fine visual art, offers performances from classical music to theater to folk shows. The Guild’s other venues include the famous Byrdcliffe Theater, and the Byrdcliffe Barn, both housing performances, while the organization maintains many programs for visiting artists, fellowships, as well as having shows of outdoor sculpture on its property, and exhibitions of fine craftsmanship, as part of its traditional heritage.

Woodstock is rich with galleries. Up on Rock City Road, you’ll find the Lotus Gallery and Photosensualis Gallery; Bernard Gerson runs BMG on Tannery Brook Road; Christina Varga is host to Varga Gallery’s eclectic offerings out on Tinker Street by Upstate Films; Evolve Gallery is across from the Woodstock Playhouse; Elena Zang shows beautiful work at her gallery on Route 212 in Shady. For information on these and others, see ulsterpub.staging.wpenginechamber.com, or call 845-679-6234. l






The Frying Pan is one of the few areas around New York City-owned Ashokan Reservoir open to the public without a hiking or fishing permit granted by the reservoir administration. The “handle” of the pan is a long, paved walkway that starts at a circular parking lot and extends along the reservoir dike, open to sweeping views of water and sky. People of all ages stroll, skate, or bicycle down the level pathway while ducks cavort in the water and occasionally deer graze the sloped lawn along the other side of the dike.

The far end of the walkway joins Reservoir Road near an area frequented by a pair of bald eagles that can sometimes be seen nesting in a tree or flying over the water. Bring binoculars if you want to look for eagles, a hat to protect from the sun (there’s no shade whatsoever), and warm enough clothes for the often strong wind.

The Frying Pan is located on a dead end road on the north side of Route 28A, about one mile east of Monument Road.

For a more strenuous hike, try the Ashokan High Point trail, an eight-mile trek to the top of the highest mountain in Olive. Highlights of the trip include gorgeous views, a classical brook, and, in the right season, blueberries. Hiking time is estimated at four and a half hours over a moderately difficult trail.

To reach the High Point trailhead, take Route 28A from Boiceville, turn onto Watson Hollow Road, and drive 3.8 miles to a parking area on the right. The trail begins across the road and to the east of the parking lot. Cross the wooden bridge and sign in at the register.


Antiques, bargains, and the patter of auctioneer Eric Borjeson are featured at the 28 Exchange in Shokan, where auctions are held about twice a month. A handsome cabinet might sell for $75, a marble-topped coffee table for $50, a sewing machine for $10, a wooden sled for $5, a carton of tchotchkes for $2—it all depends on who’s bidding.

To find out when auctions are scheduled, go to www.auctionzip.com and search the auctioneer directory for 28 Exchange, located at 3216 Route 28 just west of Winchell’s Corners (the intersection of Route 28 and Reservoir Road).

You can dance your heart out at Ashokan Center, where fiddle-guitar duo Jay Ungar and Molly Mason have been holding fiddle-and-dance camps for years. This summer’s programs include swing music, contra dance, and old-time Cajun music. Also an outdoor education center, Ashokan offers both overnight accommodations and commuter prices. It is set in a region of spectacular gorges and has historic structures dating from its days as a farm and mill site. For details, see www.ashokancenter.org.

-Violet Snow






Feeling adventurous? Heat getting to you? Try riding down the Esopus River on an inner tube. There are two tubing businesses in Phoenicia that will set you up with a life jacket and an inflated rubber doughnut with a wooden seat roped to the bottom to protect your fanny. A truck or bus is available to drive you upriver, and then you will glide or plummet on the current, possibly whooping and hollering, until you reach town. Or if you’re a novice, you can start from town and float more sedately down the less rocky stretch to Mt. Pleasant, where you will be picked up and brought back to Phoenicia.

F & S Adventures is at 29 Main Street, and the Town Tinker is at 10 Bridge Street. Check their respective Facebook pages for details of river conditions to see if tubing is available on a given day.

Hiking trails can be found all over Shandaken, but if you’re looking for a hike that’s full of interest and not too long, there’s a trailhead right in Phoenicia. On the far side of the Phoenicia Park, located behind the post office on Ava Maria Drive, is a small bridge that leads to the Tanbark Trail. It traverses the base of a sheer cliff, skirts a hemlock grove that was once a source of bark for tanneries, and climbs to an overlook that offers a splendid view of a little toy town that appears to be Phoenicia, nestled among the mountains.

If the one-mile loop that leads across the overlook is too tame for your taste, you can branch off to a longer and steeper trail that will bring you to another high ledge with an equally spectacular view. Just follow the blue Tanbark Trail markers to a sign that will point you in the right direction.

Even if you’re here to commune with the gods of nature, you might get a hankering for a culture fix. Phoenicia boasts two art galleries (Cabane Gallery and Arts Upstairs) and a theater (STS Playhouse) that produces several plays each year and shows a classic film on the last Friday of each month. Phoenicia Phirst Phridays are held every month at Arts Upstairs, with music, a poetry open mic, and a short play reading. Check out Woodland Valley Books, above the ice cream shop, for used books and the occasional poetry reading. And of course, there’s the Phoenicia International Festival of the Voice on the first weekend of August.

History buffs will enjoy a self-guided tour of Pine Hill, at the western end of Shandaken, where Victorian, Italianate, Gothic Revival, and other architectural styles remain from the heyday of the Catskill resorts in the late 1800s and early 1900s. Four local structures are already on the National Register of Historic Places, and by the time you read this, the town may be designated a National Historic Site. Admire the Morton Library, a stone building from 1903; the former hotels with their wraparound porches; two arched stone bridges; and the elegant homes, many of which were once boarding houses. Tour booklets will be available at local shops.

You might also want to visit the Shandaken Historical Museum, which is housed in a former school building at 26 Academy Street. Its intriguing collection includes vintage photographs, tools, furniture, and other artifacts. But hours vary with the seasons, so call 688-3116 to find out when it’s open.

Reach Pine Hill by driving west on Route 28. Eleven miles from Phoenicia you’ll see signs for the turnoff to Main Street.

If your kids like trains, take them on a ride with the Catskill Mountain Railroad. A vintage locomotive draws two fully restored antique passenger coaches on a five-mile round trip between Mt. Tremper and Boiceville. Trains run on weekends from Memorial Day through Columbus Day, departing from Mt. Tremper Station, located on Route 28, 22 miles from Kingston and about a mile west of Route 212.

At this time, trains do not go through to Phoenicia, due to track damage from Hurricane Irene, but it’s a quick drive to the Phoenicia train station, where the Empire State Railway Museum exhibits model trains and historical photos of Phoenicia’s railroading past.