Things to Do in Westchester County This Weekend - Events Guide 2025
Looking for things to do in Westchester County this weekend? From Hudson River waterfront concerts and historic estate tours to farmers markets and family festivals, this guide helps you discover the best weekend activities across Westchester's vibrant towns.
Best Weekend Activities by Town
Ossining: Arts, Waterfront & Community Events
Ossining offers an exceptional weekend experience combining arts, outdoor activities, and community celebrations. Start Saturday morning at the Ossining Farmers Market (year-round, 9am-2pm) for fresh local produce, artisan breads, and handmade goods. Explore exhibitions and workshops at the Ossining Arts Center, a cultural hub presenting visual arts, performances, and classes throughout the year.
The renovated Ossining waterfront hosts free summer concert series Friday and Saturday evenings with spectacular Hudson River views. The waterfront park provides walking paths, fishing pier, and picnic areas perfect for afternoon relaxation. Downtown Main Street features independent restaurants, cafes, and shops for dining and browsing. The Old Croton Aqueduct trail offers scenic walking and cycling through town.
Tarrytown: Historic Estates & Music Hall
Tarrytown combines world-class performing arts with magnificent historic sites. The Tarrytown Music Hall presents concerts, comedy, and film screenings in a beautifully restored 1885 theater—check their weekend schedule for current performances. Visit Lyndhurst Mansion, Sunnyside (Washington Irving's estate), or Philipsburg Manor for tours, seasonal events, and programs exploring 19th-century history.
Saturday mornings bring the Tarrytown Farmers Market to Patriots Park (May-November, 8:30am-1:30pm) with Hudson Valley farmers and artisans. Stroll Main Street's shops, galleries, and restaurants. The waterfront Pierson Park offers Hudson River views and hosts summer concerts and community events. Combine cultural attractions with excellent dining options throughout the village.
Peekskill: Arts District & Paramount Theater
Peekskill has emerged as a premier arts destination in the Hudson Valley. Second Saturday Gallery Walk (monthly, 6-9pm) transforms downtown into a celebration of visual arts with over 40 galleries, studios, and creative spaces open for exhibitions, receptions, and live performances. The Paramount Hudson Valley Theater presents Broadway shows, concerts, comedy, and film in a spectacular Art Deco venue—weekend performances draw visitors from throughout the region.
The Peekskill Farmers Market at Riverfront Green (Saturdays 8am-1pm, May-November) offers fresh produce and artisan goods with Hudson River backdrop. The waterfront hosts summer concert series, outdoor movies, and festivals. Explore downtown restaurants representing diverse cuisines from around the world. The Hudson Valley Center for Contemporary Art presents innovative exhibitions for art enthusiasts.
Sleepy Hollow: Legendary History & Halloween
Sleepy Hollow offers unique experiences rooted in Washington Irving's legendary tale. Visit Philipsburg Manor, a restored colonial working farm with living history programs, craft demonstrations, and seasonal celebrations. Tour the Old Dutch Church and historic cemetery where Washington Irving, Andrew Carnegie, and other notable figures are buried. October transforms the village with Halloween events including the Great Jack O'Lantern Blaze and Horseman's Hollow.
Year-round, the Sleepy Hollow Farmers Market at Barnhart Park (Saturdays 8:30am-1pm, June-November) brings local food to the community. Kingsland Point Park on the Hudson River offers beaches, trails, and summer concerts with water views. Combine historical exploration with contemporary community events throughout the year.
Yonkers: Museums, Waterfront & Urban Attractions
Yonkers, Westchester's largest city, offers diverse weekend activities. The Hudson River Museum features art exhibitions, planetarium shows, historic Glenview Mansion tours, and special events—one of the region's premier cultural institutions. Untermyer Park and Gardens showcases spectacular Persian-style gardens with Hudson River views, offering tours and concerts in magnificent settings.
The Yonkers Riverfront hosts festivals, concerts, and outdoor events throughout warmer months. The Getty Square Greenmarket (Thursdays) and weekend markets provide fresh local food. Cross County Shopping Center offers retail and entertainment options. The city's diverse restaurant scene reflects its multicultural population with authentic international cuisines.
Croton-on-Hudson: Nature & Outdoor Recreation
Croton-on-Hudson excels in outdoor recreation and natural beauty. Croton Point Park, a 500-acre county park jutting into the Hudson, offers hiking trails, beaches, camping, nature center, and diverse habitats for exploring. Guided nature walks teach about local ecosystems and wildlife. Summer brings outdoor concerts to the waterfront setting with spectacular river views.
The Croton Farmers Market (Fridays 3-7pm, June-October) at Barent Park provides end-of-week fresh food shopping with live music. The Old Croton Aqueduct trail offers scenic walking and cycling through the village. The community emphasizes environmental stewardship with numerous sustainability-focused programs and events throughout the year.
Dobbs Ferry: Village Charm & Waterfront
Dobbs Ferry offers quintessential Hudson River village experiences. The waterfront park hosts summer concert series with river views—bring blankets and picnics for sunset performances. The Dobbs Ferry Farmers Market operates year-round (Sundays 8:30am-2pm), maintaining community connections and fresh food access through all seasons.
Stroll walkable Main Street with independent shops, cafes, and restaurants. The Old Croton Aqueduct provides scenic trail walking through the village. Summer brings outdoor movies, community festivals, and waterfront celebrations. The compact, charming downtown invites leisurely weekend exploration combining shopping, dining, and riverside relaxation.
Weekend Activities by Interest
Farmers Markets & Local Food
Westchester County farmers markets operate Thursdays through Sundays throughout the region. See our complete farmers markets guide for schedules, locations, and what to expect at 12+ markets across the county. Markets offer fresh produce, artisan foods, prepared meals, flowers, and handmade goods while creating community gathering places.
Historic Sites & Museums
Hudson Valley historic sites provide fascinating weekend exploration. Lyndhurst Mansion, Sunnyside, Philipsburg Manor, and other National Historic Landmarks offer tours, special programs, and seasonal events. The Hudson River Museum, Ossining Arts Center, and Hudson Valley Center for Contemporary Art present exhibitions and cultural programming. Many sites host concerts, festivals, and educational programs beyond regular tours.
Outdoor Recreation
The Old Croton Aqueduct trail runs through multiple Westchester towns offering 26+ miles of scenic walking and cycling. Croton Point Park, Blue Mountain Reservation, and numerous other parks provide hiking, picnicking, and nature observation. Hudson River waterfront parks in every town offer walking paths, fishing, and water views. Spring through fall bring ideal conditions for outdoor activities.
Live Music & Performing Arts
Summer weekends feature free outdoor concert series at waterfront parks across Westchester. The Tarrytown Music Hall and Paramount Hudson Valley Theater present year-round professional performances including concerts, comedy, Broadway shows, and film. Local venues host acoustic music, jazz, and contemporary acts. Gallery Walk events often include live music and performances.
Family-Friendly Activities
Playgrounds, splash pads, and parks throughout Westchester provide spaces for children's recreation. Many historic sites offer hands-on programs for kids. Farmers markets feature children's activities. Libraries host storytimes and craft programs. Summer brings outdoor movie nights, festivals with kids' zones, and special family programming at cultural institutions.
Seasonal Weekend Highlights
Spring (March-May)
Farmers markets reopen for outdoor season. Gardens and historic estates showcase spring blooms. Earth Day events celebrate environmental stewardship. Outdoor recreation resumes as weather warms. Memorial Day weekend brings parades and ceremonies honoring veterans.
Summer (June-August)
Outdoor concert series perform at waterfront parks. Farmers markets operate at peak season with abundant local produce. Beaches and swimming areas open. Historic sites host outdoor events on extensive grounds. Art fairs and craft shows take advantage of pleasant weather. Independence Day brings fireworks and celebrations.
Fall (September-November)
Autumn foliage creates spectacular scenery for outdoor activities. Harvest festivals celebrate the season. Halloween transforms Sleepy Hollow with themed events and celebrations. Farmers markets feature fall produce including apples, pumpkins, and winter squash. Concerts and performances return to indoor venues. Holiday shopping begins at markets and craft fairs.
Winter (December-February)
Holiday celebrations include tree lightings, caroling, and festive markets. Indoor farmers markets maintain year-round food access. Cultural institutions present exhibitions, concerts, and programs. Historic sites offer holiday tours and seasonal programming. Theaters present winter performance seasons. Indoor activities dominate as outdoor recreation becomes more limited.
Planning Your Westchester Weekend
Getting Around
Metro-North Hudson Line provides excellent rail access to Westchester towns from New York City and within the county. Most towns feature walkable downtowns once you arrive. Driving between towns takes 10-30 minutes depending on locations. Parking is generally available at major venues and municipal lots. Some visitors enjoy multi-town exploration taking advantage of Westchester's compact geography.
Best Times to Visit
May through October offers peak outdoor season with farmers markets, concerts, and festivals in full swing. Fall foliage (late September through early November) provides spectacular scenery. December brings holiday celebrations. Each season offers distinct experiences and activities suited to different interests and weather conditions.
Insider Tips
- Check event calendars before visiting—many weekend programs require advance tickets or registration
- Arrive early at popular farmers markets for best selection
- Combine multiple activities in one town to maximize your weekend
- Consider staying overnight to experience evening performances and explore more leisurely
- Follow venue social media for last-minute schedule changes or additions
Stay Informed About Weekend Events
Hudson Life Dispatch's free weekly newsletter delivers curated weekend event recommendations every Friday morning. Never miss concerts, markets, festivals, or special programs happening across Westchester County and the Hudson Valley. Subscribe to get personalized recommendations and discover hidden gems in your favorite towns.