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Late Summer Events in the Cortlandt, NY and Hudson Valley Area

Bannerman Castle

With the end of summer just around the corner, there's no better time to take advantage of the beautiful warm weather before another frigid Westchester winter takes hold. Luckily, plenty of fun, family-friendly activities take place in and around the Cortlandt area that can make the perfect outing for a September or October day.

Our team members at Bill Volz Westchester put together this list of four of the most popular late-summer events you and your family can enjoy over the next two months in the Hudson Valley. We've also included locations and contact information, so you can find as many details as possible before solidifying plans to savor the last bit of summer.

Movie Nights at Bannerman Castle

The first summer events on our list of the best outings in the Cortlandt and greater Hudson Valley area are Movie Nights at Bannerman Castle. Bannerman Castle is an abandoned military arsenal just 50 miles north of New York City on Pollepel Island, where it stood from 1901 until an unfortunate fire led to its abandonment in 1969. Luckily, a Hudson Valley local started the Bannerman Castle Trust in 1992, which led to the castle's restoration and current status as a popular tourist attraction for guests ages 12 and up.

Nowadays, locals and visitors alike can take an evening cruise to and from the island to discover the castle's unique history and enjoy classic movies on the island with a one-of-a-kind backdrop. Catch the Estuary Steward before it departs from the Beacon Waterfront at 5 p.m. and 6 p.m. to get a scenic ride to the island. You can purchase various concessions on the island, and restrooms are also available. Here's a breakdown of the September 2022 Movie Nights and Bannerman Castle schedule, along with the movies they'll project for the audience to enjoy:

  • Friday, Sept. 2, 2022 — "Little Shop of Horrors."
  • Friday, Sept. 23, 2022 — "Young Frankenstein."
  • Friday, Sept. 30, 2022 — "Hunchback of Notre Dame."

Location: 2 Red Flynn Drive, Beacon, NY.

Phone: 845-831-1001.

Taste of RMV

One of the most beloved summer events in the Cortlandt area is none other than the Taste of RMV festival at the Red Maple Vineyard here in the Hudson Valley. This annual tradition offers some of the best food, wine, cider, and beer in the region, all of which you can sample at affordable prices. Enjoy farm-to-table delicacies representing traditions from around the world, with popular items on the tasting menu including Vietnamese mango veggie rolls, Mediterranean-inspired falafel pita sandwiches, Indian veggie samosas, and house-smoked pork shoulder Mexican tacos.

You can complement some of these delicious food items from the tasting menu with house-made specialty cocktails, including a grapefruit rosemary mule, red and white peach sangrias, and strawberry mojitos. A vast selection of white and red wines, ciders, and beers are also available, along with non-alcoholic options like apple cider, fresh fruit juices, and still and sparkling waters direct from Saratoga. Taste of RMV also includes live music, pop-up art shops, and outdoor movie showings that are sure to be fun for people of all ages.

Location: 103 Burroughs Drive, West Park, NY.

Phone: 845-834-6050.

SeptemberFest Street Fair

The next event taking place this summer in the Hudson Valley region is the annual SeptemberFest Street Fair in nearby Nyack, New York. The SeptemberFest Street Fair is a great family-friendly outing filled with fun activities that people of all ages can enjoy. The fair features over 200 local vendors selling hand-crafted items, including jewelry, art, photography, antiques, and crafts, so there's something for everyone, regardless of age or interests.

Sample food and drinks from some of Nyack's most beloved dining establishments in a safe outdoor atmosphere and dedicate some time to exploring local restaurants and pubs in the area. The event also features live entertainment, including music performances from local artists. No pets are allowed at the fair, and all attendees must abide by CDC COVID-19 protocols. The SeptemberFest Street Fair will take place on Sunday, Sept. 11, from 10 a.m. to 5 p.m., rain or shine.

Location: Main Street & Broadway, Nyack, NY.

Phone: 845-353-2221.

Kids' Craft Connection

The final spot on our list of the top late summer events taking place in and around Cortlandt, New York, is the Kids' Craft Connection at the historic Boscobel House and Gardens. Kids can enjoy a flashlight tour of the Boscobel mansion and its 68 acres of land, including immaculate gardens and a woodland trail. Enjoy a photo op on the mansion's Great Lawn, which offers a one-of-a-kind view of the Hudson River. Activities include reenactments of historic chores, games, and crafts that make the perfect souvenir.

Kids' Craft Connection takes place once a month throughout the summer and early autumn months, with events on Saturday, Sept. 10 and Oct. 8. Admission is $13 for children and $24 for adults, with advance ticket reservations recommended for ensuring entry. Each month has a different theme, so you and your family can enjoy updated activities and crafts each time you visit. This event is best for children ages 5 and up.

Location: 1601 Route 9D, Garrison, NY.

Phone: 845-265-3638.

So, there you have it. Those are our top four picks for late summer events in the Cortlandt, New York, area. We hope this article comes in handy the next time you and your loved ones are searching for a fun activity in the Hudson Valley this September and October. Did we leave out one of your favorite summertime events in the region? Have a suggestion for a future community-based article? Shoot us a line at Bill Volz Westchester, and we'll be happy to take down your content suggestions.

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Photo Credits: Bannerman's Island by Nick Harris is licensed by CC BY-ND 2.0

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The atmosphere is approachable, and the wood-fired pizza angle gives it extra appeal when you want a snack or meal with your drink. During nice weather, the sidewalk bier garden feel adds to the experience, giving guests a simple way to enjoy Croton’s village charm. For Cortlandt-area residents, this is a nice option when you want something relaxed and close by. It is also a good stop before or after a walk around Croton-on-Hudson, a visit with friends, or a low-key summer evening that does not require a big plan. Downtown Peekskill Energy at Whiskey River NY Whiskey River NY brings a different kind of summer sipping experience to the list. Rather than a brewery-only stop, it is a downtown Peekskill restaurant and bar with a lively, welcoming feel. This is a good choice when the group wants food, drinks, and a social atmosphere in one place, especially if not everyone is strictly focused on craft beer. Whiskey River NY serves American food with a creative twist, plus a beer menu, cocktails, and a setting that works for everything from dinner with friends to a casual night out. Its location on North Division Street puts it in one of Peekskill’s most walkable areas, which is a major plus during the summer. You can grab a meal, enjoy a drink, and continue exploring nearby shops, music spots, or riverfront areas without feeling rushed. This is also a practical pick for people who want a hangout rather than a traditional taproom. The menu gives you more flexibility, the drinks cover a wider range of preferences, and the downtown setting makes it feel connected to the local scene. For Cortlandt residents, it is close enough for a spontaneous weeknight dinner but lively enough to feel like a weekend destination. Community-Minded Craft Beer at Sing Sing Kill Brewery Ossining’s Sing Sing Kill Brewery is a strong choice for craft beer drinkers who care about local character. This NY Farm Brewery and taproom has a clear community identity, with house-made beer, local values, and a welcoming taproom environment. It feels deeply tied to the Hudson Valley, which gives it a different kind of charm than a more commercial beer stop. Sing Sing Kill Brewery brews beer on the premises and offers a range of styles, along with guest taps and other New York-made beverages. Its focus on sustainability and community programming adds another layer to the experience. For many visitors, that makes the beer feel connected to something bigger than the glass in front of them. This is a great summer stop for people who enjoy a taproom with personality. It works for a relaxed afternoon, a casual meetup, or a visit after spending time in Ossining or along the Hudson. The Ossining location is also a nice change of pace for Cortlandt-area residents who want to explore nearby towns while still keeping the trip simple and local. Gather Around at Round Table Brewery Round Table Brewery in Garnerville is a little farther from Cortlandt than some of the Peekskill and Croton stops, but it is still worth considering for a summer craft beer outing. The brewery has a warm, social identity built around good beer, community, and gathering with friends. It is a natural fit for people who enjoy destinations that feel like more than a quick stop at the bar. Round Table Brewery offers a tavern and brewery experience in Garnerville, with beers, Argentine-inspired cuisine, and events helping shape the atmosphere. The brewery side focuses on quality brews, including traditional and mixed fermentation methods, while the tavern gives guests a comfortable place to settle in. It is a good option for a group outing, especially when the goal is to eat, drink, and spend a little more time together. For those coming from Cortlandt, the drive can feel like part of the adventure. It gives you a reason to explore another Hudson Valley community while still staying within reach of home. If your summer plans include brewery hopping or finding new places to gather with friends, Round Table is a strong addition to the list. Make the Most of Summer Near Cortlandt The area around Cortlandt has plenty of ways to enjoy a summer afternoon or evening without traveling far. River Outpost Brewing Co. brings the waterfront brewery feel, The Croton Tapsmith offers small-town craft beer charm, Whiskey River NY adds downtown Peekskill energy, Sing Sing Kill Brewery brings Ossining community spirit, and Round Table Brewery makes the trip to Garnerville feel worthwhile. Together, they show how much local flavor can be found within a short drive of Cortlandt. Bill Volz Westchester CDJR is proud to be part of a region where local businesses, scenic drives, and community gathering spots help make everyday life more enjoyable. Next time you are planning a summer outing near Cortlandt, these breweries and hangouts are great places to start.