Fall has arrived Out East. Mornings start with a walk by the water, afternoons might take you to Sag Harbor or out to the vineyards, and cooler evenings are made for dinner, a good glass of wine, and a seat by the fire.
With Canoe Place as your home base, here’s how we’d spend a fall weekend in the Hamptons.
Friday: Settle In
Arrive Friday afternoon, drop your bags, and take a little time to settle into your room before heading to Good Ground Tavern. Start the weekend with a cocktail or glass of wine and dinner inspired by the season.
After dinner, head down the road to Oakland’s Restaurant to catch the sunset over Shinnecock Bay. Grab a drink, find a spot by the water, and watch the last light of the day disappear over the bay.
Then head back to Canoe Place for a glass of wine by the fire.
Saturday: Beach, Sag Harbor & a Little Rosé
Start Saturday with coffee and a pastry from Hampton Coffee Company, then head to Ponquogue Beach for the morning. The beach takes on a different rhythm this time of year—take a long walk along the water or settle into a chair with a good book and get a few chapters in by the ocean.
Head back to Canoe Place to freshen up, then set off for Sag Harbor. Spend the late morning wandering through town, stopping at a few of our favorites along the way. Browse the shelves at Sag Harbor Books, explore the garden and beautifully curated finds at Sage & Madison, then pop into Carissa’s the Bakery for a loaf of bread or something sweet for later.
By now, you’ll probably be ready for lunch. Grab a table at Sag Harbor Tavern, known for its much-loved burger, though there’s plenty more on the menu worth ordering.
From here, the afternoon is yours.
Take the scenic drive through Bridgehampton and Sagaponack to Wölffer Estate for a tasting at the Main Estate. Or, when live music is on the calendar, head to The Wine Stand for a bottle of wine, vineyard views, and an easy afternoon outside.
As evening arrives, return to Sag Harbor for dinner at Tutto il Giorno, followed by drinks at Faraway.
Back at Canoe Place, grab a cocktail at the Terrace Bar or enjoy a drink in the garden at Good Ground Tavern.
Or, Spend Saturday on the North Fork
For a different taste of the East End, trade the day in Sag Harbor for a day exploring the North Fork with North Fork Sights, Bites & Flights.
This privately guided experience brings together local wineries, seasonal food, farms, artisans, and coastal stops, all tailored to your interests. Reservations, tastings, meals, and chauffeured transportation are taken care of, so you can simply enjoy the day.
Our Guest Services team can help personalize your itinerary and arrange all the details
Closer to Home
There’s plenty to do without leaving Canoe Place. Spend the morning in the kitchen at Good Ground Tavern, cooking alongside Executive Chef Mathew Woolf and his culinary team. The private experience is shaped around your tastes and what you’d like to learn, with a seasonal main course and dessert on the menu.
Once the cooking is done, sit down together for lunch and a glass of wine or cocktail, then leave with a Canoe Place apron, your recipe, and a few new tricks to try at home.
Throughout the fall, you can also join us for wine tastings and cocktail classes—an easy addition to an afternoon or evening at The Place.
Sunday: One Last Slow Morning
Start Sunday with a complimentary yoga class led by Doza Yoga in the Pavilion from 9:30–10:30 a.m., followed by breakfast on the terrace at Good Ground Tavern. Or head right around the corner to The Hampton Maid, a longtime local favorite for breakfast.
After checking out, stop in Westhampton Beach before heading home. Walk through town and browse a few local favorites, including GOOD Westhampton, Mixology, and Island Surf. Pick up a few provisions for home at Mill Road Cheese Shop or Justin’s Chop Shop, then grab a coffee from One Trick Pony for the road.
There’s still plenty of September left to enjoy Out East.
