Three miles west of Red Hook , in Annandale-on-Hudson, is Montgomery Place (River Rd., off Rte. 9G, 845/758-5461 or 800/448-4007, www.hudsonvalley.org , house closed for renovations, grounds open 10 a.m.–5 p.m. Sat.–Sun. May–Oct., free admission). One of the loveliest mansions along the Hudson, this quiet, 1802 Federal-style gem was remodeled in the 1860s by the famed Alexander Jackson Davis, and every line of the classical structure, every inch of the romantic grounds seems perfectly in its place. From the mansion’s circular, columned portico are stunning views of the Hudson and the Catskills  beyond.
For almost 200 years, Montgomery Place was home to the prominent Livingston family. Members of the family continued to live in the house until the 1980s, and it is still almost entirely furnished with their treasures.
Surrounding Montgomery Place are landscaped grounds laced with walking trails. Just outside the estate’s gates are its still-thriving Montgomery Place Orchards (845/758-6338), where you can pick your own fruits and berries June–October.
Abutting Montgomery Place is Bard College (Rte. 9G at Annandale Road, 845/758-6822, www.bard.edu ), an idyllic 540-acre campus peppered with gardens and wooded groves. Once owned by Columbia University in New York City , Bard is now an independent institution known for its creative arts programs.
Cutting-edge exhibits are showcased in the Center for Curatorial Studies (845/758-7598, 1–5 p.m. Wed.–Sun., free admission). Concerts and the critically acclaimed Bard Music Festival (which each year studies a different composer) are presented in the dramatic, brushed-stainless-steel Richard B. Fisher Center for Performing Arts (845/758-7900), designed by architect Frank Gehry and acoustical designer Yasuhisa Toyota. Tours of the center, whose swooping lines reflect the surrounding landscape, are offered at 11 a.m., 1 p.m., and 2 p.m. most days of the year.
The SummerScape SpieglTent (845/758-7900, www.bard.edu/pac/summerscape ) is a can’t miss burlesque show, modern dance, modified performing circus, and dj-led venue. Check website for schedule.