Southampton's Best Fall and Winter Activities

Southampton, NY, offers a variety of delightful activities to enjoy throughout the fall and winter. From scenic pumpkin picking to festive holiday events, each activity offers its own charm. Let’s dive into some of the top seasonal activities near Southampton that will make these cooler months memorable.

Apple and Pumpkin Picking at The Milk Pail U-Pick Farm

Just a short drive from Southampton to Water Mill, The Milk Pail U-Pick Farm is a fall favorite for locals. Open Friday through Sunday, this spot is perfect for picking fresh apples and pumpkins. Don’t leave without grabbing their famous apple cider donuts and a gallon of freshly pressed cider – a must-try seasonal treat. This is an ideal family outing that brings the essence of autumn to life.

Explore Montauk Lighthouse

On cooler days, visiting Montauk Lighthouse offers scenic views and history wrapped into one adventure, just a one-hour drive from Southampton. Enjoy a meal at George’s Lighthouse Café, located nearby, which serves local dishes with a panoramic ocean backdrop. The lighthouse area is especially breathtaking at sunset, and you can catch live music on select weekends during the fall.

Winter Art at The Parrish Art Museum

When the chill of winter sets in, cozy up indoors with art at The Parrish Art Museum in Water Mill, a short drive from Southampton. This museum offers rotating exhibitions and special programs throughout the winter months. Attending an artist talk or guided tour is a great way to stay warm while engaging with Southampton’s vibrant art scene.

Winter Walks at Mashomack Preserve

Just a ferry ride away on Shelter Island, Mashomack Preserve transforms into a winter wonderland. With miles of trails to explore, it’s perfect for a brisk winter hike. Bundle up and enjoy the peaceful surroundings as you walk through snowy woodlands and along scenic waterfronts.

Holiday Shopping in Southampton Village

Southampton Village comes alive with festive cheer during the holiday season. Explore the beautifully decorated streets, enjoy hot cocoa from local cafes, and find unique gifts at the boutique stores. Many shops offer seasonal deals and special events, making holiday shopping in Southampton an enjoyable experience.

Enjoy the Season in Southampton

From outdoor adventures to indoor festivities, Southampton and its surrounding areas offer something for everyone in the fall and winter. And if you need reliable transportation to get around and enjoy all that Southampton has to offer, stop by Mercedes-Benz of Southampton to find a vehicle that’s perfect for your next adventure. Enjoy the season, and make the most of these special months!