What to Do

Activities In Town

AROUND THE LAKE - Takes about 45 minutes, relatively flat. Start from the house (turn right at the end of the driveway) and walk around the lake. Turn right onto Beach Road on the small bridge when you come to the Lake Road/Beach Road fork. Keep left and walk up the hill with the town baseball park on your right (you can alternatively walk down to the town beach and playground). Walk up Stissing Avenue, turn right at Poplar Avenue, right again when you hit Lake Road.STISSING MOUNTAIN FIRE TOWER - New York 12567. Try this 1.8-mile loop trail with a breath-taking view at the top. Walking distance from the house. It is somewhat steep and can be challenging depending on the weather. Takes an average of 1 hour to complete for those in shape, two hours if taking your time. The view from the watchtower on the peak is spectacular! This is a popular trail for birding, hiking, and walking.THOMPSON POND NATURE PRESERVE - Short distance from the house. Great walk/hike for the whole family. Beautiful 2.7-mile loop trail.MASHOMACK FISH & GAME PRESERVE - Pine Plains, NY 12567. World class polo in a beautiful setting. Weekend tailgates and fancy dress up pavilion. Check out the polo schedule here: https://www.mashomackpoloclub.com/schedule.htmlHAMMERTON BARN 3201 NY-199, Pine Plains, NY 12567 (518) 398-7075. One of my favorite home goods shop. Fabulous country decor with just the right amount of sophistication. Great gifts!RONNYBROOK FARM. 310 Prospect Hill Rd, Pine Plains, NY 12567. (518) 398-6455. Considered the “Dom Perignon” of dairy by the NY Times. Ronnybrook welcomes visitors to see how their cows are cared for, tour the barn where "the ladies" spend much of the cold northeast winter months, or watch as they bottle the milk, make butter, or culture their artisan yogurts.CHASEHOLM FARM CREAMERY 100 Chase Rd, Pine Plains, NY 12567. (518) 398-0368 Siblings Sara and Rory Chase operate 3rd generation certified organic and grass-fed creamery. Farm store sells raw milk, beef, veal, sauerkrauts, farmstead cheeses. Favs include Nimbus, a triple cream cow's milk cheese.

Four Brothers Drive In

Hiking

Mashomack Polo

Ronnybrook Farms

In & Around The Hudson Valley

Arts and Entertainment

The Stissing Center, 2950 Church St, Pine Plains, NY 12567, (518) 771-3340. For upcoming events: https://TheStissingCenter.org The Stissing Center offers many types of events, Live Music, Drama, Film and Community Events.The Moviehouse - 48 Main Street Millerton, New York 12546 518.789.0022. This all-digital, independent theater shows a mix of blockbusters, prestige dramas, and scrappy indies across its multiple screens, with reserved seating in theaters 1, 2, and 3. It also displays art and has hosted local authors and filmmakers for special talks. If you need to relax or want to keep quiet for an hour or two, The Moviehouse is worth a stop.Lyceum Cinema. 15 Old Farm Rd, Red Hook, NY 12571. Six screens, bargain matinee pricing with Holy Cow across the street!Four Brothers Drive-in - 4957 NY-22, Amenia, NY 12501, (845) 373-8178. It’s hard not to love this place: not only are there outdoor movies, of course, but the food and drinks are far better than the typical popcorn and soda. For a main meal, there are two (equally stellar) options: the superb, gooey pizza at Four Brothers Pizza Inn, or the classic diner fare at The Grand Shack, like juicy double cheeseburgers or the TJ’s dog with bacon sauce. Save room for dessert: the Nutella milkshakes are famous for good reason.Ro-Lin Lanes Inc - 3974 NY-9G Red Hook, NY 12571

Golf

Red Hook Golf Club - 650 NY-199 Red Hook, NY 12571

Hiking

I love to hike and these are some of my favorites!APPALACHIAN TRAIL Level of difficulty: Somewhat strenuous Distance: 48.4 Miles in CT; I’ve hiked the AT from CT, NY to MA and suggest choosing a section to attack. This is great resource: https://www.outdoors.org/resources/amc-outdoors/adventures/section-hiking-the-appalachian-trail-in-connecticut/www.nynjtc.org/park/appalachian-national-scenic-trailwww.dutchess.org/hiking/pawling_appalachian_trail It looks like a vintage movie set, but the tiny wooden train platform created specifically for Appalachian Trail hikers, about two miles outside of Pawling, is for real and operates on weekends and holidays. Don’t be fooled: The trail from the train station starts out easy and flat along a lovely wooden boardwalk over Great Swamp wetlands brimming with birds and frogs. Fields and forests follow, but then comes the whammy: a steep ascent to Cat Rocks that is rewarded with pretty, panoramic views.ANTHONY'S NOSE NY 10524 Level of difficulty: 6 out of 10 (steep, short climb) Length and time: 2.6 miles; 2.5 hours; 792 ft Feet Cumulative Gain Relatively short hike to an awesome Hudson River overlook. BREAKNECK RIDGE TRAIL - Cold Spring, NY 10516 Level of difficulty: Intense, Length and time: Almost 3 miles long; allow 4+ hours http://nynjtc.org/hike/breakneck-ridge-trail Challenging rock scramble in the Hudson Highlands State Park Preserve that offers spectacular views of Storm King Mountain and Bannerman’s Castle from cliff overlooks. Insider tip: Don’t bring small children or your dog (unless you can carry them), as many find it hard to scale the steep spots. CASTLE ROCK - Philipstown, NY 10524 Level of difficulty: Moderate Distance and time: About 7 miles; at least 4 hours www.nynjtc.org/hike/east hudson-highlands-5 Part of Hudson Highlands State Park, this route is easily reached by taking the Metro North Hudson Line to the Garrison station and following the trail to the parking lot. Carriage roads and wooded trails take you on a picturesque hike with highlights that include a gazebo, several stream crossings, rocky outcrops, and lovely views of the Hudson and Bear Mountain Bridges. For part of the hike, you’ll be on the Appalachian Trail. DOVER STONE CHURCH - 3128 NY-22 Dover Plains, NY 12522 Level of difficulty: Easy Distance and time: A little over one mile round-trip, so budget an hour—or more if you want to hike the side trails http://townofdoverny.us/Stone_Church.cfmGERTRUDES NOSE - NY 12525 Level of difficulty: Perfect for new hikers who are up for a challenge, experienced hikers looking for a moderate day Length and time: 6 miles long; allow 4-6 hours Arguably the most picturesque vista in the Shawangunks, Gertrude's Nose is a geologic snapshot of the destructive natural forces that are slowly ripping apart the Shawangunk conglomerate and leaving behind some of its most intriguing features. Traverses six miles of stunning views and fascinating geological formations and is a combination of wide carriage roads and rocky footpaths. HARLEM VALLEY RAIL TRAIL Level of difficulty: Moderate Distance: About 10 miles; One of the earliest in the region, this excellent rail trail heads south out of town along the Webatuck Creek, passing 10.7 miles through roads, woods, and fields before reaching the Wassaic Station. Unpaved and undeveloped sections have been purchased, with the goal of extending it for 46 miles, all the way to Chatham. It’s a pleasant walk and an easy round trip by bike.MOUNT BEACON FIRE TOWER - Beacon, New York 12508 Level of difficulty: 5-10/ 10 (depending on how far you choose to go) Length and time: : 2.4 miles,1.5 hours (overlook), or 4.4 miles, 3 hours (overlook + re tower), or a big fat 7.7-mile, 5.5 hours beast of a loop that hits the overlook, re tower and more Awesome views, rebuilt tower, incline railroad ruins, choose-your-own adventure difficulty STORM KING MOUNTAIN - New York 12520 Level of difficulty: Perfect for novice hikers looking for a challenge and experienced adventurers Length and time: 6.5 miles; 1,500 Feet Cumulative Gain Explore one of the west Hudson's treasures with views spanning far up and down the Hudson River, Breakneck Ridge and West Point, the summit is well worth the effort.

Horseback Riding

Rivendell Riding Academy, 2591 Salt Point Turnpike, Clinton Corners, NY 12514, (845) 266-3334, Great barn for children to learn how to canter, ride, and trot along the local trails atop a friendly steed.
Pine Plains Equestrian Center, 2054 Rt. 83 Pine Plains, NY 12567 (518) 398-1034http://www.pineplainsequestrian.com/ (I am not sure if this has re-opened since covid.

Skiing

Catamount - 78 Catamount Road Hillsdale, NY 12529 Catamount ski mountain runs a great adventure ropes and zipline course in the summer as well as skiing and snowboarding in the winter. Also downhill mountain bike trails. http://www.catamountski.com/

Mansion Tours

If you are a history buff, you'll love visiting some of the finest examples of architecture, landscaping, and interiors, from the early Federal period to the numerous revival styles of the late 19th and early 20th century showcased in the meticulously restored and lovingly maintained Estates of the Hudson Valley.

http://www.hudsonriver.com/hudson-river-estates

Rafting

Clarke Outdoors rents rafts and kayaks to paddle the beautiful Housatonic River in Northwestern Connecticut about 40 minutes away. (860) 672-6365. They can rent canoes and rubber rafts for self-paddling or for guided group runs. Please call them in advance as their rafts and trips get booked up.

Roller Skating

Wood'n Wheel is the place to go for roller skating, laser tag, bumper cars, wall climbing, Ulster Park, NY. http://www.woodnwheel.com/

Skiing

Catamount - 78 Catamount Rd Hillsdale, NY 12529 Catamount ski mountain runs a great adventure ropes and zipline course in the summer as well as skiing and snowboarding in the winter. Also downhill mountain bike trails. http://www.catamountski.com/

Wineries

There are a number of wineries nearby where you can go for tastings. Millbrook Vineyards (Route 82 south of Pine Plains) Clinton Vineyards (Route 82 south of Pine Plains) Cascade Mountain Winery & Restaurant (Amenia)

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