About 12 miles northeast of Poughkeepsie  on Route 44 is sleepy yet moneyed Millbrook, surrounded by large estates and horse farms. Though it seems hard to believe today, in this village of pricey antique stores and gift shops, Timothy Leary once ran his League for Spiritual Discovery out of the old Danheim estate on Franklin Avenue.
The estate, located about a mile from the village green, is recognizable by its large stone gatehouse built in Bavarian style. Others who’ve made Millbrook their home in more recent years are Mary Tyler Moore, Daryl Hall, and Liam Neeson.
One of the oddest sites in the Hudson Valley  is the whimsical Wing’s Castle (717 Bangall Rd., off Rte. 44 northeast of Millbrook, 845/677-9085, noon–4:30 p.m. Wed.–Sun. June–Dec., adults $7, children $5), set atop a rolling, lime-green hill with a panoramic view of the Hudson Valley. Built by Peter and Toni Wing and family, the castle is a 30-odd-year-old work-in-progress, lovingly put together out of everything from antique barn doors to toilet-bowl floats. Much of its stone came from abandoned railroad bridges.
It all began in the late 1960s when Peter, just back from Vietnam, and his wife Toni needed a place to live. They owned a piece of land, but had only $1,100 between them. The solution? They’d build the place themselves, out of salvaged materials; never mind the fact that they had no construction experience whatsoever.
Everyone told them it couldn’t be done, but today the castle stands, quirky and proud. Each part is designed in a different style—Asian, Tibetan, Germanic, French—and it all works beautifully, with bits of colored fiberglass winking in the walls and a water-filled moat leading to an inviting hot tub. Inside is a hodgepodge collection of military artifacts, carousel animals, Native American arts, and the Wings’ personal possessions.
Landscaped around a small glacial lake just outside Millbrook is the serene 200-acre Innisfree Garden (362 Tyrell Rd., one mile off Rte. 44 west of Millbrook, 845/677-8000, www.innisfreegarden.org , 10 a.m.–4 p.m. Wed.–Fri. and 11 a.m.–5 p.m. Sat.–Sun. May–Oct., admission $4 on weekdays, $5 on weekends, children under 6 free). Founded by painter Walter Beck and his wife Marion, and designed according to Eastern principles, the so-called “cup garden” is actually a series of many little gardens, each arranged to draw attention to one especially beautiful object at its center.
One of the small gardens focuses on a lotus pool, another on a group of “purple smoke trees,” a third on a hillside cave. On a spit of land jutting out into the lake are the Dragon, the Turtle, and the Owl—three large rocks standing sentinel over the preserve.
Despite the garden’s careful design, it has a wild and natural feel. Spreading out over a series of small hills and dales, dappled by sunlight, it features many isolated spots where visitors can dreamily linger.
A few miles west of Millbrook is a 1,900-acre preserve that’s home to both the Flagler Cary Arboretum (Rte. 44A, just off Rte. 44, 845/677-5359, 9 a.m.–4 p.m. Mon.–Sat. and 1–4 p.m. Sun., with extended hours to 6 p.m. daily May–Sept., free admission) and the Institute of Ecosystem Studies (Rte. 44A, just off Rte. 44, 845/677-5343, www.ecostudies.org , trails sunrise–sunset daily and internal roadways 8:30 a.m.–7 p.m. daily Apr.–Oct.). The arboretum is open to the public, as is much of the institute’s grounds, where ecological research is being conducted. Both are connected to the prestigious New York Botanical Garden in New York City .
Visitors to the arboretum must stop first at the Gifford House Visitor and Education Center to pick up a visitor permit, information, and maps. Directly behind the center are the perennial gardens, filled with over 1,000 species of plants. Among these gardens is a daffodil bed with 12 kinds of daffodils, a poisonous plants bed, and a garden specifically planted to attract butterflies. Surrounding the gardens are short hiking trails that lead past meadows, fern glens, and pine and hemlock forests.
Spread out over 50 acres just below Wing’s Castle is Millbrook Vineyards (26 Wing Rd., at the Shunpike/Rte. 57, 845/677-8383 or 800/662-9463, www.millbrookwine.com , noon–5 p.m. daily). Millbrook is especially known for its chardonnay, but it also produces a pinot noir, merlot, and other wines.
About 10 miles northeast of Millbrook is the award-winning Cascade Mountain Winery and Restaurant (835 Cascade Mountain Rd., Amenia, 845/373-9021, www.cascademt.com , 11 a.m.–5 p.m. Sat.–Sun.). The chalet-style restaurant is open for lunch Wednesday–Sunday (average lunch entrée $9); restaurant is closed January–February. To reach the winery, take Route 44 east to Cascade Mountain Rd.
Camping is available at the 40-site Wilcox Memorial Park (Rte. 199, off the Taconic Pkwy., Stanfordville, 845/758-6100, $25 tent, $32 trailer with electric and water).
The refreshingly down-to-earth A Cat in Your Lap (Rtes. 82 and 343, 845/677-3051, ($85 d in the main house; $120 d for the studios in the barn) is a B&B housed in a gracious 1840s farmhouse and a converted barn.
The vintage, stainless-steel Millbrook Diner (3266 Franklin Ave., village center, 845/677-5319) serves dependable diner fare and especially good breakfasts.
Foremost among the area’s more serious eateries is Allyn’s Restaurant and Cafe (42–58 Rte. 44 midway between Millbrook and Amenia, 845/677-5888, $22), which always offers a few regional specialties along with more general innovative American fare on its huge menu.
Nearby Serevan Restaurant (6 Autumn Lane on Route 44, West of Route 22 Amenia, NY 12501,845/373-9800, Thursday–Monday, dinner, $25) earns raves from diners for Chef Serge Madikians’ Mediteranean-Middle Eastern fusion flair, enhanced by local organic and free range elements.