A Cozy Autumn Escape in Sag Harbor, New York

A Cozy Autumn Escape in Sag Harbor, New York

Tucked away on the eastern tip of Long Island, Sag Harbor is a charming town nestled between Southampton and East Hampton. Known for its vibrant summer scene, it transforms into a serene, cozy haven when autumn arrives.

This fall, I set off on a road trip to experience the quieter, more laid-back side of Sag Harbor—apple picking, sipping local wines, and soaking up all the warm, autumnal vibes. As I explored, I couldn’t help but wonder: could the Hamptons be the perfect destination for a fall escape?

Getting to Sag Harbor from New York City is a scenic three-hour drive, though travel time can vary with traffic. As the leaves start to change, the route becomes especially beautiful, making it an ideal autumn road trip. While there are also bus and train options available, we chose to rent a car from the airport (taking the subway there first). This gave us the flexibility to explore at our own pace, from visiting nearby beaches to checking out other towns throughout the Hamptons.

Fall Activities

Milk Pail U-Pick Farm: Apple picking at Milk Pail is a fall activity that should not be missed. Strolling through the orchard, surrounded by the colors and scents of autumn, is a vibe. Admission for up to 6 people (ages 3 and up) includes a 20-pound bag (1/2 bushel) for $53 (cash) or $55.65 (credit).

Wölffer Estate Vineyard: This vineyard is an ideal spot to savor local wine in a serene setting. I highly recommend making a reservation in advance to secure a table outdoors, right next to the grapevines.

The Wine Stand: A more laid-back spot to enjoy a glass of wine, often accompanied by live music. No reservation is needed, making it easy to drop by and relax. If you're up for it, bring your own chairs and sit out on the grass next to the grapevines for a truly casual, scenic experience.

Channing Daughters Winery: Another local favorite, known for its variety of unique blends.

Walk on the Beach: The beaches may be quieter than in the summer, but they are just as beautiful. A stroll along the shore, with the cool breeze and soft sounds of the waves, is a peaceful way to start or end your day.

Eat & Drink

Lulu Kitchen & Bar: The menu highlights flavors centered around wood-fired cooking. Be sure to try their signature dishes—the roasted cauliflower and crème brûlée are must-haves.

Tutto il Giorno: A seaside restaurant with outdoor seating, known for serving authentic pasta dishes. Even during the off-season, it's best to book a reservation to secure a spot.

Page 63 on Main: A bistro offering classic American cuisine.

Vin Sur Vingt Wine Bar: A cozy place to unwind and sip on some wine.

Goldberg’s Famous Bagels: A go-to spot for delicious breakfast bagels and sandwiches. Established in 1949, this iconic shop originated in Brooklyn, Queens, and other parts of New York before expanding out to the Hamptons.

Murf’s BackStreet Tavern: A laid-back local dive bar, perfect for late-night drinks and a taste of the local scene.

The Restaurant at Baron’s Cove: A classic American dining experience, serving elevated twists on traditional Long Island cuisine.

Jack’s Stir Brew Coffee: A good spot to grab your coffee fix, also offering cold brew—a must-have for fans of iced coffee like me.

Accommodations

While Sag Harbor doesn’t have many big-name hotel options, there are plenty of charming inns and B&Bs. We chose to rent an Airbnb located within walking distance of the main street, giving us easy access to shops, restaurants, and coffee spots. The area is very walkable, and we loved being able to explore without having to drive everywhere.

As the summer crowds fade, Sag Harbor transforms into a peaceful, cozy retreat. The crisp autumn air, vibrant foliage, and seasonal harvest events create an idyllic setting for a fall getaway.

Whether you’re savoring wine at a vineyard, strolling along the quiet beaches, or indulging in a warm meal at a local spot, there’s a unique charm that autumn brings to this picturesque town.

Visited last in October 2024