Take the Trolley

After your visit to Dia:Beacon, hop aboard Beacon's Main Street Trolley (Fri-Sun) for a spin through town and check out the city's self-described "Renaissance on the Hudson." The trolley makes several stops along Main Street (hop on and off all afternoon for $2), but be sure to check out the charming East End antiques district and the contemporary galleries that dot Main Street. Highlights include Collaborative Concepts (348 Main), Concentric Gallery (174 Main), and the brand-new Hudson Beach Glass, housed in a restored firehouse at 162 Main St. Note: If the trolley isn't running during your visit, it's just a 1-mile drive to downtown.

Hyde Park Discounts & National Parks Passes

With the purchase of admission to both the Vanderbilt estate and Roosevelt home, library, and museum, a third visit, to either of the Roosevelt retreats, Val-Kill or Top Cottage, is free.

These historic sites in Hyde Park belong to the extensive network of national parks. Several new discount passes are available to visitors, including the National Parks and Federal Recreation Lands Annual Pass, $80 (individuals; good for 1 yr.), and Interagency Senior Pass, $10 (for seniors only; lifetime membership). Older passes, including National Parks Passes, Golden Eagle, Golden Eagle Hologram, Golden Access, and Golden Age Passports, will continue to be honored according to the provisions of the pass. All park passes, good for free entry to any Vanderbilt-Roosevelt historic site tour, can be purchased at the national park sites in Hyde Park. For more information, see www.nps.gov or http://store.usgs.gov/pass.

Walk Across the Hudson

Claiming to be the longest pedestrian bridge in the world, the landmark 1888 Poughkeepsie Railroad Bridge (tel. 845/454-9649; www.walkway.org), now known as "Walkway Over the Hudson," had its grand reopening in October 2009. The 6,767-foot (1.25-mile) bridge, the longest in the world when it was inaugurated, is now a "linear park," open to walkers, cyclists, joggers, and people with disabilities, connecting to rail trails and parks on both sides of the river. It stretches from Poughkeepsie, on the east side of the Hudson, to the town of Lloyd on the west side.

Especially for Kids

Kids will love the Rhinebeck Aerodrome, with its vintage airplanes and cool air shows. In Kingston, families can take a Hudson River cruise out to the lighthouse or hop aboard a vintage trolley car. Some of the great estates have extraordinary grounds and gardens with trails through the property; check out the Vanderbilt Mansion, Staatsburgh, and Montgomery Place. And finally, as an educational supplement to history classes, take the kids to Washington's Headquarters in Newburgh and the FDR Presidential Library and Museum in Hyde Park.

Wine Trails & Farmers' Markets

The Hudson Valley, the nation's oldest winemaking region, is today home to about three dozen wineries. Though few of the area's wineries have yet attained national followings, a number of them offer tours and tastings, and several are blessed with outstandingly scenic locations. If you'd like to visit a winery or two during your stay, all you have to do is follow the trail -- either the Dutchess Wine Trail (tel. 845/266-5372; www.dutchesswinetrail.com), on the east side of the Hudson, or the Shawangunk Wine Trail (tel. 845/255-2494; www.shawangunkwinetrail.com), on the west side of the river. More than a dozen are open to regular visits. The following is merely a selection of my favorites: The Dutchess (Country) Trail consists of Cascade Mountain Winery, 835 Cascade Mountain Rd., Amenia (tel. 845/373-9021), which has a lovely setting and a very nice little restaurant with outdoor seating; Clinton Vineyards, Schultzville Road, Clinton Corners (tel. 845/266-5372), makers of a pretty nice white, a Seyval blanc; Alison Wines & Vineyards, 231 Pitcher Lane, Red Hook (tel. 845/758-6335), with a garden shop, baked goods, and cut-your-own Christmas trees on the premises; and Millbrook Vineyards & Winery, 26 Wing Rd., Millbrook (tel. 800/662-WINE), the largest and one of the best of the lot. Millbrook makes an excellent pinot noir reserve, offers a full tour, features art exhibits and live music on Saturday nights in summer, and is worth the visit for the views over the rolling hillsides and horse farms alone.

Several of the nine family-owned wineries of the Shawangunk Trail, all sandwiched between the Shawangunk Mountains and the Hudson River in Ulster County, are easily visited on a Hudson Valley trip. Among them are Brotherhood Winery, 35 North St., Washingtonville (tel. 845/496-9101), the oldest winery in the United States, in operation since 1839. Though the winery doesn't grow its own grapes (instead importing them from Long Island, the Finger Lakes, and California), its grounds constitute a well-stocked campus, with vast underground vaulted cellars and a whole host of shops and activities on-site. Claiming to be the oldest continuously operating vineyard in the U.S. is Benmarl Wine Company, 156 Highland Ave., Marlboro-on-Hudson (tel. 845/236-4265; www.benmarl.com), a small, family-owned independent with awe-inspiring views from a hilltop location on the west side of the Hudson (btwn Newburgh and New Paltz). It also offers a small gallery of the owner's illustrations and artwork; Mark Miller was one of the best-known magazine illustrators in the world in the 1940s and 1950s. Schedules for winery tours and tastings vary, though most are open to visitors throughout the Memorial Day-to-Labor Day season; for current hours and events, check the trail websites or pick up a brochure at any tourism information outlet.

Farmers' markets and pick-your-own farm stands are everywhere in this beautiful, bucolic region. There are dozens and dozens, so here are just a few: Mead Orchards and Farm Stand, 25 Scism Rd., Tivoli (9 miles north of Rhinebeck; tel. 914/756-5641), with pick-your-own apples and pumpkins; Greig Farm, Pitcher Lane, Red Hook (tel. 914/758-1234), which has pick-your-own fruits and vegetables and a farm market; Millbrook Farmers' Market, Franklin Avenue at Front Street, Millbrook village, every Saturday from 9am to 1pm; and Tarrytown Farmers' Market, Patriot's Park, Route 9, Tarrytown (tel. 914/923-4837). Ask around and locals will come up with many more.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.