The New York State Thruway (Interstate 87), a divided toll road, is the primary route to the Catskill region for visitors coming from the south and southeast (i.e., New York City and its suburbs). As signs along the highway inform you, Exits 16–21, roughly 45–113 miles (72–185 km) from the city, serve the Catskills.
The most convenient highway to the central Catskills, New York State Route 28, begins at Kingston. After getting off the Thruway at Exit 19, you'll bear right into the traffic circle and see the Catskill Park welcome sign before you cross the Thruway and head west. Route 28 is the preferred route to the central Catskills, including the villages of Woodstock and Phoenecia.
New York State Route 17, a freeway in the process of being converted to Interstate 86, begins its westward journey at Thruway Exit 16 in Harriman.
On Route 17, bout an hour and fifteen minutes north of the Thruway interchange in Woodbury, (and just over two hours from the Bronx), is the village of Roscoe, NY. At this point, and for the next 35 or so miles northbound, the highway not only provides a southerly access to the Catskills (as it has since crossing the Shawangunk Ridge), but it is now truly within the Catskills, with all it's scenic beauty.
Route 206 begins in Roscoe, and heads generally northwest, through Delaware County, and on to Greene, NY and then to Whitney Point, NY at Interstate 81. Route 206 is the access route to the quietest towns (Downsville, Walton, Masonville, Franklin) of the quietest county (Delaware County) that the Catskills has to offer.
Exit 21 on the Thruway provides the most direct access to the Escarpment and the tall peaks of the Blackhead Range, the Catskills' third, fourth and fifth-highest mountains, loom off to the side of the Thruway. Here New York State Route 23 makes a slow climb up the north face of the Escarpment, past Five State Lookout (which lives up to its billing on clear enough days), to Windham, home to another popular ski area with that same name.
Go fly fishing - this region is home to numerous rivers hallowed by fly fisherman including the Beaverkill, Neversink, the Delaware, the Esopus, and the Willowemoc.
During summer, there are many kosher restaurants open however they are usually quite expensive. During the year, there are plenty of restaurants selling basic food items, such as pizza, burgers, and fries.
During summer, many people go into the Catskills from New York City. Some of them drive like they're still in the city, so be careful when driving.
In winter, the roads have ice and it gets very slippery.
Drive carefully on secondary and tertiary roads if you are unfamiliar with them, particularly those that are unpaved. Many of them were built to serve local farms, not visitors, so they take steep slopes and sharp turns. Should you have an accident, assistance is some distance away and will take time to arrive; cellular phone coverage may not even be available.
This advice goes doubly or triply for those roads in adverse weather conditions. Some dirt roads have signs noting that they are not maintained in wintertime. If your vehicle is not equipped with four-wheel drive it would be wise to consider an alternate route.
Interstate 88 has been known to get very windy and icy during the winter.
Heavy rainfall can also turn some of those roads into quagmires. Even paved roads are not immune, if they travel through narrow gaps between mountains at any point. NY 268 has been closed for months at a time in the wake of major storms due to flooding and landslides, for instance.
Be sure to equip yourself with the proper equipment while hiking. As a general rule and at minimum, wear sturdy, waterproof hiking boots, carry plenty of water, avoid cotton garments except during the hottest months, leave plenty of time to return to the trailhead, and expect sudden changes of weather - much more so than in coastal climates. Many hikers wear trousers (not shorts) at all times in the Catskills, there is an increasing concern over ticks, and a walk through a field of stinging nettles (a plant about knee-high with tiny stinging hairs on the leaves and stems) is an unforgettable experience.
Be aware of the various hunting seasons in the Catskills, primarily deer/rifle season, which generally extends from roughly a week before Thanksgiving to several weeks after Thanksgiving. Check the DEC website for exact details. The Catskills are in the 'southern zone' according to DEC hunting season maps. Hiking during hunting season is generally not recommended, but it is not impossible, either, if one takes the proper precautions.
Animal hazards include rattlesnakes in a small number of locations in the Catskills (primarily near Hancock and north of Woodstock), these snakes, as well as skunks and porcupines, are not much of a hazard for adults with a fair amount of situational awareness, but they could become a problem for curious children and dogs.
Crime in the Catskills region is generally concentrated in the Sullivan County cities and towns along Route 17, particularly Monticello, which can get pretty rough, especially at night. Late-night travelers to the area coming up via Route 17 should wait until they have made it to Delaware County before stopping in for gas and supplies. A great spot for a road trip meal is the Roscoe Diner, located right off the highway in the town of the same name. Once in Roscoe, continue north on Route 206 into Downsville, Walton, Franklin, Colchester or Masonville. This is truly the region's quietest area.
Many visitors from more populated area are often taken aback at the prevalence of firearms carried openly. There are several species of small game that the DEC has designated as 'open season' so be aware that there may be some hunting going on at any given time of year. Individuals who own homes or seasonal cabins in remote areas may engage in target practice on their own land, anyone can do so on public lands. If hearing shooting near a hiking trail makes you nervous, it is very reasonable to ask the individuals to stop shooting until you are well past. The simple presence of a firearm, either holstered (handgun) or safely carried (long gun) should cause a visitor absolutely no concern.