Guidebook for Woodstock, Saugerties, and Kingston

Tiffany
Guidebook for Woodstock, Saugerties, and Kingston

Food Scene

Located in a restored and rambling farmhouse at the gateway to Woodstock, Cucina boasts a contemporary Italian menu based on seasonal, local ingredients. A warm, friendly ambience centers around a modern country setting with professional yet casual service and hospitality. Open 7 nights and brunch on Saturday and Sunday. Co-owner of Cucina Lois Freedman is President of Jean George restaurants.
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Cucina
109 Mill Hill Rd
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Located in a restored and rambling farmhouse at the gateway to Woodstock, Cucina boasts a contemporary Italian menu based on seasonal, local ingredients. A warm, friendly ambience centers around a modern country setting with professional yet casual service and hospitality. Open 7 nights and brunch on Saturday and Sunday. Co-owner of Cucina Lois Freedman is President of Jean George restaurants.
Every Saturday from 10-2 May through November. Featuring local produce, meat, seafood, and eggs, along with quality prepared food vendors and select local artisans and craftspeople. With live entertainment, children's activities, and educational displays, there is going to be something for everyone!
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Kingston Farmers Market
285 Wall St
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Every Saturday from 10-2 May through November. Featuring local produce, meat, seafood, and eggs, along with quality prepared food vendors and select local artisans and craftspeople. With live entertainment, children's activities, and educational displays, there is going to be something for everyone!
Great brunch and dinner spot. Comfort food using organic and local ingredients. Our favorites are the classic grilled cheese and tomato soup & fried brussels sprouts.
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Shindig
1 Tinker St
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Great brunch and dinner spot. Comfort food using organic and local ingredients. Our favorites are the classic grilled cheese and tomato soup & fried brussels sprouts.
Saturdays 10-2 from May to November. The market offers local seasonal vegetables, luscious orchard fruits, dried herbs, fresh-laid eggs, tasty goat and cow cheeses, pasture-raised meats and free-range poultry, fresh fish and seafood, delicious maple syrup, honey, jams and sauces, pickles, and artisanal breads.
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Saugerties Farmers Market
43 Partition St
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Saturdays 10-2 from May to November. The market offers local seasonal vegetables, luscious orchard fruits, dried herbs, fresh-laid eggs, tasty goat and cow cheeses, pasture-raised meats and free-range poultry, fresh fish and seafood, delicious maple syrup, honey, jams and sauces, pickles, and artisanal breads.
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Kingston
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A must visit for foodies - can have a long wait so go early! Drive from house is about 25-30 mins wait but worth it.
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Phoenicia Diner
5681 NY-28
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A must visit for foodies - can have a long wait so go early! Drive from house is about 25-30 mins wait but worth it.
Farm-to-table fine dining that serves simple rustic fare with ingredients harvested from Hudson Valley farms and dairies. Definitely call ahead for a reservation on weekends
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SILVIA
42 Mill Hill Rd
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Farm-to-table fine dining that serves simple rustic fare with ingredients harvested from Hudson Valley farms and dairies. Definitely call ahead for a reservation on weekends
Kingston waterfront dining at 1 Broadway with outdoor seating. Lobster Bake on Thursday and Friday.
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Mariner's Harbor
1 Broadway
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Kingston waterfront dining at 1 Broadway with outdoor seating. Lobster Bake on Thursday and Friday.
Kingston Mexican eatery with plenty of outdoor seating at 97 Abeel Street, walking distance to the waterfront. Try one of their signature margaritas and mole chicken enchiladas
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Armadillo
97 Abeel Street
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Kingston Mexican eatery with plenty of outdoor seating at 97 Abeel Street, walking distance to the waterfront. Try one of their signature margaritas and mole chicken enchiladas
Creative and classic flavors such as ube health bar crunch, honeycomb chocolate swirl, and Belgian chocolate at this little shop in Saugerties
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Alleyway Ice Cream
135 Partition St
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Creative and classic flavors such as ube health bar crunch, honeycomb chocolate swirl, and Belgian chocolate at this little shop in Saugerties

Arts & Culture

Over a period of 37 years, Harvey Fite created the monumental world-acclaimed 6½-acre bluestone sculpture now known as Opus 40. Constructed by one man, using dry-key stone techniques adapted from the Mayans, Opus 40 is made from millions of pieces of indigenous bluestone, laid by hand, creating a labyrinthine world of finely fitted stone, swirling with ramps and terraces constructed around pools and trees and fountains, rising out of bedrock a half mile deep. Takes about 1-2 hours to walk the grounds.
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Opus 40
356 George Sickle Rd
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Over a period of 37 years, Harvey Fite created the monumental world-acclaimed 6½-acre bluestone sculpture now known as Opus 40. Constructed by one man, using dry-key stone techniques adapted from the Mayans, Opus 40 is made from millions of pieces of indigenous bluestone, laid by hand, creating a labyrinthine world of finely fitted stone, swirling with ramps and terraces constructed around pools and trees and fountains, rising out of bedrock a half mile deep. Takes about 1-2 hours to walk the grounds.
As an iconic site of American Theatre & Music History, the establishment of the Woodstock Playhouse by Robert Elwyn was a monumental moment in the region’s history. The site is a crown jewel of American Theatre History established in 1938 as one of the first rural extensions of Broadway with connections to Al Hirschfeld, the debut of many famous actors of pop-history, grand legends of theatre & film, Margaret Webster’s American Repertory Theatre, and musicians who became idols and voices of our generations. As home to a pivotal 1968 concert, the generally accepted precursor to Woodstock 1969, the site holds a vibrant energy as a mecca for those who embrace history, theater, and music.
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Woodstock Playhouse
103 Mill Hill Rd
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As an iconic site of American Theatre & Music History, the establishment of the Woodstock Playhouse by Robert Elwyn was a monumental moment in the region’s history. The site is a crown jewel of American Theatre History established in 1938 as one of the first rural extensions of Broadway with connections to Al Hirschfeld, the debut of many famous actors of pop-history, grand legends of theatre & film, Margaret Webster’s American Repertory Theatre, and musicians who became idols and voices of our generations. As home to a pivotal 1968 concert, the generally accepted precursor to Woodstock 1969, the site holds a vibrant energy as a mecca for those who embrace history, theater, and music.

Parks & Nature

Swimming hole that's very popular. A pretty jade lagoon surrounded by trees with a rope swing. Water is about 4 feet deep. The parking area is just a road side pull off. Once you park, you follow a well worn trail down to the water.
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Big Deep
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Swimming hole that's very popular. A pretty jade lagoon surrounded by trees with a rope swing. Water is about 4 feet deep. The parking area is just a road side pull off. Once you park, you follow a well worn trail down to the water.
Overlook Mountain Trail is a moderate difficulty 4.8 mile very popular trail located near Woodstock that features beautiful wild flowers and amazing views. At the top, you'll find the ruins of an old hotel, a sky-piercing fire tower, and a truly awe-inspiring view of the Hudson Valley. 3-hour round trip hike that can be extended to 9.3 miles to include a trip to the nearby Echo Lake.
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Overlook Mountain Trailhead
353 Meads Mountain Rd
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Overlook Mountain Trail is a moderate difficulty 4.8 mile very popular trail located near Woodstock that features beautiful wild flowers and amazing views. At the top, you'll find the ruins of an old hotel, a sky-piercing fire tower, and a truly awe-inspiring view of the Hudson Valley. 3-hour round trip hike that can be extended to 9.3 miles to include a trip to the nearby Echo Lake.
Very popular spot for swimming so I'd recommend going on weekdays and not weekends
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Little Deep
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Very popular spot for swimming so I'd recommend going on weekdays and not weekends
A top favorite for the region so definitely go early in the morning or avoid Saturdays and Sundays. Tallest 2-tier waterfall in NY, painted by many of the Hudson Valley artists
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Kaaterskill Falls Trail Head
New York 23A
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A top favorite for the region so definitely go early in the morning or avoid Saturdays and Sundays. Tallest 2-tier waterfall in NY, painted by many of the Hudson Valley artists
The Ashokan Rail Trail, or “ART,” showcases stunning views of the Ashokan Reservoir, mountain vistas, and birdlife. The ART is built upon the former Ulster and Delaware Railroad right-of-way and opens an 11.5 mile corridor to the public for the first time in over a century. Open sunrise to sunset year-round. Read more here: http://ashokanrailtrail.com
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Ashokan Rail Trail- Woodstock Dike Trailhead
1285 NY-28
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The Ashokan Rail Trail, or “ART,” showcases stunning views of the Ashokan Reservoir, mountain vistas, and birdlife. The ART is built upon the former Ulster and Delaware Railroad right-of-way and opens an 11.5 mile corridor to the public for the first time in over a century. Open sunrise to sunset year-round. Read more here: http://ashokanrailtrail.com
Onteora Lake is a small narrow waterbody that has great access and good fishing opportunities. Onteora lake is really popular with folks that like to kayak and have a small boat for fishing. Perfect picnic spot as there is a table setup overlooking the lake. Three loops of increasing ruggedness intersect to let you choose your own adventure ranging from 2.4 miles to 7 miles. It’s a 10 minute drive from our house - type in “Onteora Lake Trailhead and Parking” to find the parking lot. More info here: https://mountain-hiking.com/onteora-lake
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Onteora Lake Trailhead and Parking
Unnamed Road
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Onteora Lake is a small narrow waterbody that has great access and good fishing opportunities. Onteora lake is really popular with folks that like to kayak and have a small boat for fishing. Perfect picnic spot as there is a table setup overlooking the lake. Three loops of increasing ruggedness intersect to let you choose your own adventure ranging from 2.4 miles to 7 miles. It’s a 10 minute drive from our house - type in “Onteora Lake Trailhead and Parking” to find the parking lot. More info here: https://mountain-hiking.com/onteora-lake
Three easy to moderate trails <1.5 mile round trip with great views of the Hudson River and a quaint waterfall. Plenty of parking, 15 mins away in Saugerties
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Falling Waters Preserve
Dominican Lane
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Three easy to moderate trails <1.5 mile round trip with great views of the Hudson River and a quaint waterfall. Plenty of parking, 15 mins away in Saugerties
The rail-trail follows the route of the former Ulster and Delaware Railroad, which once carried vacationers from Kingston Point to the Catskill Mountains. ~25 min drive from the house. Easy, flat walk with beautiful views of the Hudson River. Use “Kingston Rotary Park” in Google maps and park there to access the trail. More info here: https://kingstongreenline.org/
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Kingston Point Rail Trail
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The rail-trail follows the route of the former Ulster and Delaware Railroad, which once carried vacationers from Kingston Point to the Catskill Mountains. ~25 min drive from the house. Easy, flat walk with beautiful views of the Hudson River. Use “Kingston Rotary Park” in Google maps and park there to access the trail. More info here: https://kingstongreenline.org/
Cute sand beach swimming area with a dock out in the Esopus Creek, a playground, a fishing area, a kayak launch, and restrooms. Walkable to Krause Chocolates for a root beer float and hand-dipped candies, Alleyway Ice Cream, and many shops and dining options on Main Street in Saugerties. Quaint and family-friendly, recommended excursion paired with exploring town.
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Saugerties Village Beach
47 S Partition St
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Cute sand beach swimming area with a dock out in the Esopus Creek, a playground, a fishing area, a kayak launch, and restrooms. Walkable to Krause Chocolates for a root beer float and hand-dipped candies, Alleyway Ice Cream, and many shops and dining options on Main Street in Saugerties. Quaint and family-friendly, recommended excursion paired with exploring town.
Medium-sized sand beach with beautiful views of the Hudson River. Offers Hudson River swimming, picnic area, volleyball, and playground. A lively scene with groups and families spending all-day at the beach. 102-144 Delaware Ave with a parking lot that can fill quickly on weekends. After the beach, you can drive to the waterfront and grab dinner at Armadillo or a number of other restaurant choices in the area.
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Kingston Point Beach
102-144 Delaware Ave
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Medium-sized sand beach with beautiful views of the Hudson River. Offers Hudson River swimming, picnic area, volleyball, and playground. A lively scene with groups and families spending all-day at the beach. 102-144 Delaware Ave with a parking lot that can fill quickly on weekends. After the beach, you can drive to the waterfront and grab dinner at Armadillo or a number of other restaurant choices in the area.

Drinks & Nightlife

The Barn, as it is affectionately known, began as the home recording studio of Levon Helm (drummer of the legendary rock-roots group, The Band, which performed at the original Woodstock Festival). Starting in 2004, it turned into a mini Woodstock, hosting a series of Midnight Rambles. The spontaneous shows, feature up-and-comers as well as Helm’s famous friends such as Emmylou Harris, Elvis Costello, Norah Jones and the Black Crows.
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Levon Helm Studios
160 Plochmann Ln
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The Barn, as it is affectionately known, began as the home recording studio of Levon Helm (drummer of the legendary rock-roots group, The Band, which performed at the original Woodstock Festival). Starting in 2004, it turned into a mini Woodstock, hosting a series of Midnight Rambles. The spontaneous shows, feature up-and-comers as well as Helm’s famous friends such as Emmylou Harris, Elvis Costello, Norah Jones and the Black Crows.
Amazing craft cocktails and tapas in Woodstock
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Early Terrible
45 Mill Hill Rd
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Amazing craft cocktails and tapas in Woodstock

Sightseeing

Since before the Revolutionary War, the Beekman Arms has welcomed guests to the beauty of the Hudson Valley. This historic hotel in the Hudson Valley has operated continuously since 1766, retaining much of its colonial hotel charm and character, while offering modern conveniences.
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Beekman Arms-Delamater Inn
6387 Mill St
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Since before the Revolutionary War, the Beekman Arms has welcomed guests to the beauty of the Hudson Valley. This historic hotel in the Hudson Valley has operated continuously since 1766, retaining much of its colonial hotel charm and character, while offering modern conveniences.

Entertainment & Activities

The Dutchess County Fairgrounds is the home of the annual Dutchess County Fair. Open for over 160 years, the fairgrounds are open year-round and host a number of event including the Country Living Fair, Rhinebeck Antique Show, and Hudson Valley Wine and Food Festival.
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Dutchess County Fairgrounds
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The Dutchess County Fairgrounds is the home of the annual Dutchess County Fair. Open for over 160 years, the fairgrounds are open year-round and host a number of event including the Country Living Fair, Rhinebeck Antique Show, and Hudson Valley Wine and Food Festival.
Where rescued farm animals live the good life. Goats, turkeys, and more roam free and are cared for by two former film people who used to work with Errol Morris. Free guided tours offered on the weekends.
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Woodstock Farm Sanctuary
2 Rescue Rd
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Where rescued farm animals live the good life. Goats, turkeys, and more roam free and are cared for by two former film people who used to work with Errol Morris. Free guided tours offered on the weekends.
Great live music venue with lots of outdoor events
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Colony
22 Rock City Rd
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Great live music venue with lots of outdoor events
Excellent pizzas and Italian food at this Cider Bar in Accord at 215 Lower Whitfield Road (~40 min drive). Check site for hours and events - www.westwindorchard.com
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Westwind Orchard
215 Lower Whitfield Rd
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Excellent pizzas and Italian food at this Cider Bar in Accord at 215 Lower Whitfield Road (~40 min drive). Check site for hours and events - www.westwindorchard.com
Stylish, modern boutique hotel with “Local Mondays” that offers a day pass to their pool at $25/person from 11am-5pm with a snack shack opened from 12-4pm. You have to get there early to get a spot (a little before 11am ideally), and if you don’t, you can always have lunch on site and play lawn games. Or head to Tannersville for frozen custard and burgers at Mama’s Boy Burgers.
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Scribner's Catskill Lodge
13 Scribner Hollow Rd
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Stylish, modern boutique hotel with “Local Mondays” that offers a day pass to their pool at $25/person from 11am-5pm with a snack shack opened from 12-4pm. You have to get there early to get a spot (a little before 11am ideally), and if you don’t, you can always have lunch on site and play lawn games. Or head to Tannersville for frozen custard and burgers at Mama’s Boy Burgers.

Getting Around

17-minutes drive from our house. Buses run roughly on the hour to/from New York City Port Authority
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Kingston Trailways station
400 Washington Ave
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17-minutes drive from our house. Buses run roughly on the hour to/from New York City Port Authority
10-minute drive from our house. Buses don't run as frequently as to Kingston so please check schedule
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Pine Hill Trailways
4 Mill Hill Rd
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10-minute drive from our house. Buses don't run as frequently as to Kingston so please check schedule
Amtrak station at Rhinecliff is about 25 minutes from the house
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Rhinecliff Station
455 Rhinecliff Rd
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Amtrak station at Rhinecliff is about 25 minutes from the house