Weekend Wonders: Your Guide to Fun in Dutchess County (May 2–4, 2025)
Debbie Allan May 1, 2025
Debbie Allan May 1, 2025
Friday, May 2: Expect a warm day with highs around 82°F (28°C). However, be prepared for cloudy skies and a chance of showers and thunderstorms, some of which may be severe with damaging winds, hail, and heavy downpours.
Saturday, May 3: Mostly cloudy with afternoon showers likely. Highs near 75°F (24°C). It's a good idea to have an umbrella handy if you're planning outdoor activities.
Sunday, May 4: Partly sunny and cooler, with highs around 64°F (18°C). A pleasant day to wrap up the weekend.
From Family Frolics to Nighttime Delights: Dutchess County's Weekend Lineup
Looking for exciting ways to spend your weekend in Dutchess County? Whether you're planning a family outing, a romantic evening, or a solo adventure, there's something for everyone. Here's your curated guide to the best events happening from Friday, May 2, through Sunday, May 4, 2025.
Rhinebeck Antique Car Show & Swap Meet
📍 Dutchess County Fairgrounds, Rhinebeck
🗓️ May 2–4, 2025
Car enthusiasts and families alike will enjoy this annual event featuring classic cars, parts vendors, and memorabilia. It's a great opportunity to teach the kids about automotive history and enjoy a day outdoors.
👉 Learn more
Toddler Time at Bounce Sports & Entertainment
📍 Poughkeepsie
🗓️ May 2, 10:00 AM – 3:00 PM
Designed for children under 5, this event offers a safe and fun environment for little ones to jump, play, and socialize.
👉 More info
Hudson Valley Renegades Baseball Game
📍 Dutchess Stadium, Wappingers Falls
🗓️ May 3, 6:35 PM
Enjoy America's pastime with the whole family as the Renegades take on their rivals. Fireworks will follow the game, making it a night to remember.
👉 Get tickets
Live Music at The Chance Theater
📍 Poughkeepsie
🗓️ May 2, 8:00 PM
Catch local bands and enjoy a night of live music at this iconic venue. The lineup includes rock, indie, and alternative acts.
👉 Event details
Wine Tasting at Millbrook Vineyards & Winery
📍 Millbrook
🗓️ May 3, 12:00 PM – 5:00 PM
Sip on award-winning wines while enjoying live jazz music and stunning vineyard views. A perfect date idea or a relaxing afternoon with friends.
👉 Visit website
Spring Market at Vassar College
📍 Poughkeepsie
🗓️ May 4, 10:00 AM – 4:00 PM
Support local artisans and vendors at this spring market featuring handmade crafts, organic produce, and live performances.
👉 More info
Guided Hike at Ferncliff Forest
📍 Rhinebeck
🗓️ May 3, 9:00 AM
Join a guided hike through scenic trails and learn about the local flora and fauna. Suitable for all skill levels.
👉 Trail details
Be Green Kids Consignment Sale
📍 Fishkill Recreation Center
🗓️ May 2–4, 2025
Find great deals on gently used children's clothing, toys, and gear. It's a sustainable way to shop for growing kids.
👉 Sale info
Make the most of your weekend in Dutchess County with these diverse and engaging events. Whether you're exploring with family, enjoying a night out, or seeking cultural enrichment, there's something to delight everyone.
Note: Event details are subject to change. Please check the event websites for the most current information.
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I am ready to work with you to help you sell or buy a home! So whether you are a first time buyer, relocation buyer, investor, moving up or downsizing...I am ready to roll up my sleeves to go to work for you! Make your next move with Debbie Allan!