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

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

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

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

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


Camping

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.