Things to Do in The Great Outdoors of the Hudson Valley


The Catskills are home to some of the most diverse hiking in the northeast, with natural attractions that include waterfalls, lakes and spectacular views that span the northeast. From the top of the nearby Overlook Trail you can see five states on a clear day! 

Our innkeeper Karen is an avid outdoor enthusiast and is always happy to discuss recreation options near Woodstock, NY with guests.

The protected Catskill Park provides all levels of hiking trails. For the more adventurous hiker there are 35 peaks greater than 3,500 feet. (Karen is a proud member of the elite Catskill Mountain 3,500 Club having successfully climbed all the top peaks, as well as a few in wintertime – read her blog about it here! And her experiences on the popular Devil’s Path left a real impression on her, which she shares in another blog.

As one of New York’s popular trails, Overlook, is right in Woodstock. At the 3,150 foot summit of this wide, dirt trail offers views of both the Hudson River and the Ashokan Reservoir which is the source of New York City’s drinking water.

Also, the local Woodstock Land Conservancy offers monthly events for all ages on the first Saturday of the month. From paddling to hiking these guided tours are both informative and fun.

The Catskills beauty is embraced year-round by hiking enthusiasts. Winter offers expansive views, while blooming trees highlight spring’s regeneration. Summer trees offer leaf-filled shady canopies, and in the fall, trees frame the trails in colorful bursts of yellows, reds and orange.

Guests seeking to arrange independent but guided private hiking tours are encouraged to contact Karen in advance. She is familiar with many local guides and can make appropriate connections for all hiking levels.


The rolling hills and country roads of Woodstock are a bicyclist’s (and motorcyclist’s) dream come true as you can truly experience the beauty of the region close up and intimately. While many roads offer a variety of challenges for all levels of adventuresome cyclists, there are also many organized bike rides and recreational outings for those who prefer to go with a group.

Options range from an established 60-mile hilly road route to a friendly, paved flat three-mile trail, the area offers a bounty of options.

Guests who don’t want to travel with bikes also have rental choices, whether you seek an on-road or off-road adventure.  Whatever you need on two wheels, Overlook Mountain Bicycles right in town has the perfect offering. From toddling kids to the oldest kid at heart, they’ll get you all set up and offer great advice on the best places to ride. Heck, they even rent car carriers if you really want your riding experience to take you deep into the Catskills.

For guests with a valid motorcycle license, Woodstock Harley Davidson also offers rentals. Contact the store directly for more information.


Winter in Woodstock offers many ski options – both downhill and cross country. We are pleased to partner with Belleayre Ski Resort which is perfect for families and groups with diverse ski levels, as they offer everything from beginning to black diamond trails. Lessons are available, as well as a snow-centered child-care so adults can ski and toddlers can enjoy a day on the mountain. Guests at The Woodstock Inn on the Millstream can enjoy discount lift tickets to Belleayre. When making your reservation, contact us directly to confirm availability, as this is a popular program. And remember that Belleayre’s new, state-of-the-art, snow-making capacity allows the mountain to be open even when there is not snow elsewhere.

Hunter Mountain, 40 minutes from the inn, offers a more challenging ski facility, with experienced skiers tackling some of the most demanding terrain in the Catskills.

Cross country skiing and snow-shoeing provide some of the most peaceful and enjoyable ways to enjoy winter in the Catskills. Woodstock has many trails and open spaces where people of all ages can enjoy this sport. Ask Karen for guidance, as trail quality depends on seasonal conditions. Rental equipment is usually available in town.

Kayaking and Canoeing

The lakes, rivers and streams of the Catskills offer some of the most scenic water experiences in the Northeast.

Whether you’re new to kayaking or want to explore the mighty Hudson River up close, the nearby Kenco Outfitters has a program for you.

In summer the City of Kingston offers Saturday paddles from Kingston Point. These guided tours include a chance to see osprey, eagles and other local wildlife, as well as offer a historical perspective of the area’s once popular brick-building industry. The tours are appropriate for all ages, although advance reservations are suggested.

People with their own non-motorized boats can visit Onteora Lake, right off Route 28, just east of Woodstock. Upper Pond at the Kenneth Wilson park outside of Bearsville has boat rentals available. Both are operated by the DEC and offer popular, flat-water options for paddling.

In Saugerties, the Malden boat launch leads directly to the Hudson River, while a day trip along the gentle Esopus Creek can begin at Village Beach.

And of course, tubing is always popular in summer. Visit the Town Tinker tube rental in Phoenicia for more information, as conditions change frequently.


Flyfishers flock to the Catskills every year. The headwaters of the Esopus Creek are active from early spring with Rainbow to late fall with Browns. For updates on stream conditions, visit Catskill Flies or on your way into the inn stop by our friends at Kenco Outfitters on Route 28, and they will have the latest information, as well as any equipment rentals you may need.

The Catskills has a rich history of fishing, from guided outings, to week-long guy getaways. The lure of fishing was evident when city folks flocked to the mountains in pre-air-conditioned days, and the men would take to the stream to pass many an enjoyable day. While lifestyles and cooling options have changed since then, the streams – and fish –  have not. In fact, many of our local restaurants boast fresh-caught trout on the menu.