Begin your trip at Bethel Woods Center for the Arts (866/781-2922) in Bethel, located at the site of the historic 1969 Woodstock Festival. The Center offers a variety of performances by nationally renowned classical, rock, country, pop and jazz artists. (Check schedule) Enjoy the multimedia telling of the story of the 1960s and the Festival at the Museum at Bethel Woods.
Take Rte 17B west to Callicoon. Visit the Apple Pond Farm & Renewable Energy Education Center (845/482-4764), an organic horse-powered and renewable energy farm featuring tours, wagon rides, farm vacations, and more. From Callicoon, take Rte 97, the Upper Delaware Scenic Byway,for beautiful views and runs along the Delaware River. Enter the Village of Hancock where you can stop for a bite and beverage at the Hancock House Hotel. (607/637-7100)
From Hancock, take Rte 17 east, to East Branch, where you will turn onto Rte 30 north. Follow along the East Branch of the Delaware River to the Village of Downsville. Here you can take a leisurely canoe or kayak ride from Al's Sport Store and stay over at the Downsville Motel (607/363-7575), or just continue on your way where the road winds along the shores of the scenic Pepacton Reservoir. Follow Rte 30 north through Margaretville to the Town of Roxbury, where you can dine at the Public Lounge (607/326-4026) with seriously fun cocktails and captivating video screens. Overnight at The Roxbury (607/326-7200), a new "boutique motel" offering an innovative contemporary twist on the usual country lodging experience.
Have breakfast in Roxbury, talk stroll through Kirkside Park - summer destination of the Gould dynasty or visit John Burroughs Memorial Field & Woodchuck Lodge (845/586-4973), or take bike ride or stroll on the Catskill Scenic Rail Trail or horseback ride at Stone Tavern Farm (607/326-3600). Not that outdoorsy? Head back down Route 30 to Margaretville and along Rte 28 to the town of Arkville, where you'll have plenty of breakfast choices including dining in a caboose! Stroll the main street shops or antique stores. If you're into a little more shopping, head a little further east on Rte 28 to Mount Tremper and The Emerson Country Store at Emerson Resort & Spa (845/688-2828). Browse country shops in a renovated 1841 barn and view colors of a different nature through the "world's largest kaleidoscope."
Take Rte 28 east to Rte 42 north to Rte 23A east into the town of Hunter. Have lunch at Bear Creek Restaurant & Recreational Park (518/263- 3839) and enjoy spectacular mountain views while playing miniature golf. Make sure to take the scenic chairlift ride to the top of Hunter Mountain.
Continue east on Rte 23A. Just after the town of Haines Falls look for signs and a parking area for Kaaterskill Falls. Take a challenging one-mile round trip hike to see the highest two-tiered waterfall in New York State.
Continue east on Rte 23A to I-87, the NYS Thruway, and head south to Kingston. Dine at The Armadillo Bar and Grill (845/339-1550), with its Southwestern cuisine. Overnight in Kingston.
Visit the Old Dutch Church (845/338-6759), first built in 1659 and rebuilt in the 1700s. The site contains the grave of George Clinton, New York's colonial governor from 1743 to 1753.
Next, visit the Hudson River Maritime Museum (845/338-0071), the only museum in New York State exclusively dedicated to preserving the maritime heritage of the Hudson River. Stroll through the old boat shop; after, visit the historic 1913 Rondout Lighthouse.
Take Rte 28 west and then Rte 209 south to the town of Hurley and stop at Gill Corn Farm (845/338-0788). Select seasonal vegetables, pumpkins and more. Try out their delicious home-baked goods and ice cream. Fall festival weekends in October feature hayrides, pumpkin painting, and more.
Take Rte 209 north, Rte 28 west and Rte 375 north into Woodstock. Visit the Woodstock Guild/Byrdcliffe Art Colony (845/679-2079), possibly the oldest continuously-operating arts and crafts colony in the nation. If you're more adventurous, hike to the top of the fire tower on Overlook Mountain and see Woodstock below, the surrounding Catskill Mountains, the Hudson River, and even the Berkshire Mountains.
Lunch at Woodstock's organic Garden Café on the Green (845/679-3600), or Joshua's (845/679-5533), or just stroll the streets, galleries and shops of Woodstock. Perhaps enjoy a streamside or fireside meal at the Bear Café (845/679-5555).
APPROXIMATE MILEAGE: 203 miles