Pleasantville New YorkATTRACTIONS & THINGS TO DO
Listed below are the best attractions and things to do near Pleasantville, New York.
1. Rockefeller State Park Preserve
EXPANSIVE NATURAL LANDSCAPE
Rockefeller State Park Preserve offers miles of scenic carriage roads winding past woodlands, wetlands, and rolling meadows. Visitors can enjoy birdwatching, fishing, walking, and horseback riding throughout this tranquil preserve. The park is a year-round favorite for nature lovers in Pleasantville, providing a peaceful retreat from city life.
2. Usonia Historic District
FRANK LLOYD WRIGHT HOMES
The Usonia Historic District is a unique residential neighborhood designed in part by Frank Lloyd Wright, featuring over 40 architecturally significant homes. While interiors are not open to the public, visitors can stroll the quiet streets to admire the modernist exteriors and distinctive community layout. This area offers a fascinating glimpse into mid-20th-century American design innovation.
3. Graham Hills Park
TRAILS AND BIKE PATHS
Graham Hills Park boasts a network of multi-use trails popular with hikers, mountain bikers, and horseback riders. Its varied terrain makes it especially appealing for intermediate to advanced mountain bikers seeking a challenge. This wooded park is a haven for outdoor recreation right on Pleasantville's doorstep.
4. Prospero Winery & Grapes
LOCAL WINERY EXPERIENCE
Prospero Winery & Grapes invites guests to sample a curated selection of wines crafted from regional grapes. Visitors can tour the facility, learn about winemaking, and purchase bottles to take home. The winery's friendly atmosphere and knowledgeable staff make it a popular stop for wine enthusiasts in Pleasantville.
5. Soul Brewing Company
CRAFT BREWERY HUB
Soul Brewing Company is a beloved local brewery specializing in small-batch, handcrafted beers. The taproom offers a cozy space to sample rotating brews and connect with fellow beer lovers. Its central location makes it a gathering spot for Pleasantville residents and visitors alike.
6. Pleasantville Dog Park
PET-FRIENDLY OUTDOORS
Pleasantville Dog Park provides a fenced-in area for dogs to play, socialize, and exercise off-leash. The park features separate sections for large and small dogs, ensuring safe fun for all breeds and sizes. It's a popular gathering place for Pleasantville's dog owners and their furry friends.
7. Jacob Burns Film Center
ART HOUSE CINEMA GEM
Jacob Burns Film Center is a five-screen art house cinema showcasing the best in American and international independent film. The center also offers filmmaking classes and special events for cinephiles of all ages. It serves as Pleasantville's vibrant cultural hub, drawing film enthusiasts from across the region.
8. Parkway Field
COMMUNITY RECREATION GREEN
Parkway Field is a popular local park featuring athletic fields, playgrounds, and open green spaces. Families often gather here for soccer games, picnics, and summer activities. The field is a staple of the Pleasantville community for outdoor recreation and social events.
9. Best Wine Purveyors
WINE SHOPPING DESTINATION
Best Wine Purveyors offers an impressive selection of wines from around the world, along with expert recommendations for every palate. The shop regularly hosts tastings and educational events, making wine appreciation accessible and enjoyable. This is a go-to spot for Pleasantville locals seeking the perfect bottle for any occasion.
10. The Lil' Chocolate Shoppe
HANDMADE SWEET TREATS
The Lil' Chocolate Shoppe tempts visitors with its array of artisan chocolates, truffles, and confections. The cozy shop is known for its quality sweets, perfect for gifts or an indulgent treat. It stands out as a quaint and delightful stop in Pleasantville's downtown.
11. Shopping
BOUTIQUES AND SPECIALTY SHOPS

Shopping in Pleasantville ranges from charming boutiques to specialty shops offering everything from handcrafted gifts to gourmet foods. Must-visit spots include The Village Bookstore for literary finds, and The Lil' Chocolate Shoppe for sweet delicacies. Pleasantville's walkable downtown makes for a relaxed day of browsing and unique discoveries.
12. Dining
CULINARY DELIGHTS

Dining in Pleasantville is a treat, with a diverse array of restaurants catering to all tastes. Popular choices include Jean-Jacques Culinary Creations for French-inspired fare, Wood & Fire Restaurant for artisanal pizzas, and Pubstreet for creative American cuisine. The vibrant food scene is a highlight of Pleasantville's welcoming downtown.
13. Hiking
SCENIC TRAIL ADVENTURES

Hiking enthusiasts will delight in Pleasantville's array of wooded and scenic trails. Top hiking spots include Rockefeller State Park Preserve for carriage paths and woods, Graham Hills Park for varied terrain, and the nearby South County Trailway for longer excursions. These trails offer tranquil escapes and opportunities for wildlife spotting.
14. Fishing
RELAXING WATERSIDE PURSUITS

Fishing in Pleasantville can be enjoyed at Rockefeller State Park Preserve's lakes and streams, which are stocked seasonally and open to catch-and-release. Additional local options include the Saw Mill River, offering peaceful angling minutes from downtown. These accessible waters make Pleasantville a great spot for both casual and committed anglers.
15. Camping
OUTDOOR OVERNIGHT OPTIONS

While Pleasantville is not home to major campgrounds, visitors can enjoy rustic camping at nearby spots like Ward Pound Ridge Reservation and Croton Point Park. Both offer scenic campsites, picnic areas, and hiking trails within a short drive from Pleasantville. These nearby parks make it easy to experience the natural beauty of Westchester County overnight.