15 Best Things to Do in Pleasantville, NY

Pleasantville, NY
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Pleasantville is a quaint village less than an hour from the busy streets of Manhattan.

Its small-town charm and proximity to New York City have made it an attractive location for playwrights, writers, and those in the literary field.

In addition, Pleasantville is also a cultural center, home of the Spanish mission-style Jacob Burns Film Center.

Nonetheless, the village offers a refreshing change of scenery from the towering skyscrapers of NYC.

If you're looking for a laid-back vacation amid the city's hustle and bustle, here are some of the best things to do in Pleasantville, New York:

Explore Rockefeller State Park Preserve

The waters of Rockefeller State Park Preserve
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Located on Phelps Way, Rockefeller State Park Preserve offers various walking, cycling, jogging, running, and horse-riding trails that take you through fields, meadows, and woodlands.

Tulip, maple, oak, and beech trees surround the park, making it a picture-perfect destination during autumn.

Dirt trail at Rockefeller State Park Preserve
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Aside from exploring the trails, visitors may also head to the streams and wetlands to find amphibians, fishes, reptiles, and other rare aquatic species.

A bird at Rockefeller State Park Preserve
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Designated as an Important Bird Area, the park boasts more than 200 bird species, perfect for birdwatchers and enthusiasts.

Over 100 native wild bee species also frequent Rockefeller State Park Preserve between spring and summer.

Bridge at Rockefeller State Park Preserve
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Catch a Movie at the Jacob Burns Film Center

The Jacob Burns Film Center on Manville Road celebrates all things film, making it one of the best things to do in Pleasantville for cinephiles and movie enthusiasts.

Housed in a Spanish mission-style building, the film center rarely shows mainstream films and instead shows documentaries, independent, and foreign language films.

As one of the most successful art houses in the state, some notable guests and speakers include Steven Spielberg, Meryl Streep, and George Clooney.

Aside from screening movies, the Jacob Burns Film Center also holds spring, summer, and winter camps for young artists to learn more about the craft.

Bike at Graham Hills Park

Graham Hills Park is a 431-acre park with miles of hiking and biking trails.

Bike trails at the park range from beginner-friendly to more aggressive ones that suit advanced bikers.

If you have children, you may bring them on easier paths.

Along the routes, get a chance to see different rock formations, rushing streams, and even local wildlife like deer and coyotes.

Although Graham Hills Park is a popular tourist destination in Pleasantville, you can still enjoy peace and solitude during the low season.

Take note that although dogs are allowed on the trails, they must be kept on their leashes for everyone's safety.

In addition, some routes may be closed or inaccessible depending on the season and current weather conditions.

Taste Delicious Sweets at The Lil Chocolate Shoppe

Satisfy your sweet tooth and head to The Lil Chocolate Shoppe!

The confectionery shop is only a few minutes from Jacob Burns Film Center, making it a perfect stopover before or after watching a movie.

The shop dates back to 1986 when it was a small store in the Rome Theater (now Jacob Burns Film Center) and has relocated to accommodate the growing demand.

Try their artisan truffles made with real Belgian chocolate and decorated to perfection.

Some truffles are also made with alcoholic drinks and seasonal ingredients like peppermint for a festive touch.

Other sweet treats at The Lil Chocolate Shoppe include chocolate-covered marshmallows, peanut butter cups, marzipan, caramels, and sweet pretzels.

Join a Cooking Class at Zwilling Cooking Studio

Put your cooking skills to the test and join a culinary class and dinner at Zwilling Cooking Studio on Marble Avenue.

The studio offers lessons on basic knife skills, simple kitchen know-how, and how to cook your favorite international dishes.

You can learn how to recreate your favorite Asian, Chinese, Italian, Mexican, Middle Eastern, and Indian dishes.

At the end of the lesson, taste the fruit of your labor over fun conversations and discussions.

If you have kids traveling with you, you may also enroll them and introduce them to simple cooking techniques and cuisines.

However, the studio also welcomes those with little culinary experience.

Zwilling Cooking Studio is open to individuals, couples, team-building activities, birthday celebrations, and even bridal showers!

Shop for Winemaking Equipment at Home Winemaker Depot

Instead of going on a wine tour or a wine-tasting session, how about creating your own wine station?

Located on Castleton Street, Home Winemaker Depot offers different equipment and ingredients for those who want to make their wine at home.

With their barrels, fillers, fermentation tubs, cleaning supplies, and chemicals, you can make your enology dreams come true!

Home Winemaker Depot started out when Prospero Winery's founder sold California wine grape varieties, helping customers produce wine at home.

After many years, the business expanded, and they sold winemaking equipment.

Aside from selling winemaking supplies, Prospero Winery hosts an annual wine competition dinner, recognizing the best homemade wines.

Go Horse Riding at Fox Hill Farm

Fox Hill Farm is a family-owned stable located on Old Sleepy Hollow Road, a few miles from Rockefeller State Park Preserve.

The farm offers horse riding lessons in indoor and outdoor riding arenas for all skill levels.

Whether you're competing in equestrian shows, riding for leisure, or just wanting to know the basics of horse riding, the trainers will accommodate your needs.

Located near miles of historic trails, Fox Hill Farm invites visitors to go on guided trail rides on horseback.

Catch amazing views of Rockefeller State Park Preserve, Stone Barns, Hudsons River, and Swan Lake on horseback.

Unwind at Lucy's Pleasantville

After a busy day exploring Pleasantville, enjoy dinner and drinks at Lucy's Pleasantville on Bedford Road.

You may also have a glass of ice-cold beer over conversations with friendly locals and regular customers.

The restaurant and bar boast some of the best pizza and burgers in the area.

They also offer fries, pretzel sticks, tacos, mac and cheese, and cheese steak.

Lucy's Pleasantville has plant-based burgers, gluten-free pizza, and fresh salad for those with special dietary requirements.

A live band also provides entertainment and music at Lucy's Garage.

Visit the Houses at the Usonia Historic District

A house at Usonia Historic District
Magicpiano, CC BY-SA 4.0, via Wikimedia Commons

A visit to the Usonia Historic District is a must for architecture enthusiasts.

The district, built from 1946 to 1964, features a series of carefully-planned homes with a mid-century modern design.  

Sol Friedman house at Usonia Historic District
Stilfehler, CC BY-SA 4.0, via Wikimedia Commons

The neighborhood's layout was planned in the sense that it would preserve most of the existing trees and avoid disrupting the original levels of the land.

True to its name, the houses in the district feature the unique Usonian house layout.

Typical Usonian houses have no attic or basement with low roofs, an open floor plan, few interior walls, and primarily use wood, stone, and glass.

Mid-century modern house at Usonia Historic District
Magicpiano, CC BY-SA 4.0, via Wikimedia Commons

The district is part of the National Register of Historic Places because of its significant contribution to American architecture.

As you wander through the Usonia Historic District, you'll find three houses designed by famous American architect Frank Lloyd Wright: the Sol Friedman House, Edward Serlin House, and Roland Reisley House.

One of the houses at Usonia Historic District
Magicpiano, CC BY-SA 4.0, via Wikimedia Commons

Shop at the Pleasantville Farmers Market

The Pleasantville Farmers Market prides itself on being the largest year-round farmers market in Westchester.  

The market dates back to 1998 when it started as a four-stand market that aimed to support Pleasantville's local economic development while promoting sustainable and locally-grown produce.

It moved to a bigger location in 2010 to accommodate its growing popularity.

The market, which takes place in Memorial Plaza, boasts over 60 vendors, selling a wide variety of fresh produce, meat, poultry, fish, seafood, dairy products, fruits, and vegetables.

You can also shop for fresh flowers, plants, and delicious baked goods.

The Pleasantville Farmers Market offers non-edible local products like kitchen tools, handcrafted soaps, cutting boards, and serving platters.

Pamper Yourself with a Massage at Sam's Happy Feet

Treat yourself with a relaxing foot and body at Sam's Happy Feet, located on Bedford Road.

The spa offers foot reflexology services ranging from 30-, 60-, to 90-minute options.

In addition, they offer 30-to-90-minute body massages to help alleviate stress and relax the muscles.

For the ultimate pampering, Sam's Happy Feet has combination treatments so you can enjoy both foot and body massages.

The spa has a convenient location near the town's restaurants, shops, and train station, making it easy for tourists to see and visit.

Go Shopping in Downtown Pleasantville

Shop for cute trinkets, souvenirs, and clothes in downtown Pleasantville.

The area has numerous shops perfect for gift shopping, souvenir shopping, or simply shopping for yourself!

At Glass Onion Originals, check out their jewelry, ceramics, glass, and wood art.

On the other hand, head to Rhoda if you're looking for trendy clothing and vintage jewelry and accessories.

The Village Bookstore, located near the Jacob Burns Film Center, is the only local independent bookstore in the area. It offers handpicked books aside from mainstream and classic titles.

Take a break at the cafes and restaurants scattered around downtown Pleasantville in between shopping trips.

Bike across the North and South County Trailways

The North and South County Trailways are part of the statewide Empire State Trail, spanning from Manhattan to the Canadian border in Rouses Point.

The Empire State Trail is also the longest multi-use trail in the country.

In Pleasantville, visitors can bike through the North or South County Trailway.

The North County Trailway is longer and offers plenty of shade.

Most of the trail is asphalt, making it easy for trail walking or running.

However, some parts may be difficult for children or beginner bikers.

On the other hand, the South County Trailway is shorter and has sections made of asphalt and concrete.

The trail may be challenging since it isn't illuminated at night or plowed during the winter.

Both the North and South County Trailways are wheelchair accessible, so tourists with mobility issues can enjoy the scenic views.

During autumn, the gold and red-hued foliage are a sight perfect for leisurely strolls.

Relax at Nannahagan Park

Nannahagan Park is the perfect destination for tourists and families who want to spend a day out relaxing and basking under the warm Pleasantville sun.

It's a great spot for jogging, running, and walking, with its paved trails and easy paths surrounding the area.

On your visit, you may even get a chance to spot turtles and ducks swimming in the lake.

Aside from its walking trails, the park also has basketball courts and a pool for those who want to break a sweat.

If relaxing is your cup of tea, you can fish at the pond.

Nannahagan Park is a family-friendly park and has a designated playground.

Children can also fish at the pond if they have adult supervision.

Try Authentic Italian Dishes at Wood & Fire

For your dose of mouthwatering Neapolitan cuisine, head to Wood & Fire on Marble Avenue.

The restaurant has over 20 years of experience, offering anything and everything Italian.

From the classic pasta choices to their charcuterie selection, this place brings the taste of Italy to Pleasantville.

Start your meal with a salad, then try their pasts, ranging from simple yet flavorful spaghetti carbonara to their hearty linguini vongole.

You can also try their hand-tossed pizza with a variety of toppings.

Complement your dish with a glass of wine, beer, or non-alcoholic drinks.

End your meal on a sweet note and taste their tiramisu, Italian donuts, or olive oil cake.

Wood & Fire also offers gluten-free, dairy-free, and vegetarian meal options.

For those with allergies or other special dietary requirements, make sure to contact the restaurant before your visit.

Final Thoughts

Pleasantville is a small village bursting with charm and activities.

Visitors can explore the historic trails at Rockefeller State Park Preserve on foot or horseback, bike across Graham Hills Park, or relax at Nannahagan Park, among many other activities.

From the busy streets of New York City, take a trip north and explore the best things to do in Pleasantville!