The Town of Chester is made of several communities in the Adirondacks around the small town of Chestertown. Other hamlets within the town boundaries include Pottersville, Friends Lake, Loon Lake, and Schroon Lake. Of the three lakes, only Loon Lake has a public beach—for the others you'll have to check into a B&B.
The lakes are the big attractions, and are all popular places to swim, fish, boat, laze about, etc. There are also several sleepy horse ranches that will be happy to set you up with lessons, or a ride through the woods. Public lands are few in the immediate area, limiting the amount of hiking opportunities.
Luna's Pizza, 6382 Main St, Chestertown, ☎ +1 518 494-7500. It's not likely that you will find a cuter pizzeria elsewhere in upstate New York. Eccentric decor, friendly staff, good panini and salads (in addition to the greatpizzas), and free Wifi make this a great stop off the Northway.edit
Main St Ice Cream Parlor, 6369 Main St, Chestertown, ☎ +1 518 494-7940, . 10AM-8:15PM daily. A cheery ice cream, soda fountain, sandwich eatery in an old Town Hall building approaching the Platonic ideal of small town main street architecture. Tears still shed for the venerable soft serve institution of Swanee's, but no one really has any right to complain with such a great ice cream parlor right in the heart of town. Good for a light meal as well, or gift shopping for that matter.$2-8. edit
O.P. Frederick's, 5064 NY-8, Loon Lake, ☎ +1 518 494-4141, . Tu-Su 4PM-10:30PM. O.P.'s can be a little pricey, but their food is consistently some of the best around, and they have a good selection of local microbrews on tap. If you like that sort of rustic old pine wood Adirondacks atmosphere, you'll be pleased.$11-30. edit
Friends Lake Inn, 963 Friends Lake Rd, Chestertown, ☎ +1 518 494-4751, . This is a charming, traditional, and rather expensive Adirondack inn on Friends Lake, with a nearby private sandy beach, kayaks, floats, canoes, and sailboats, and some outrageously good chocolate chip cookies.$350-450. edit