Fall is the perfect time of year for a weekend getaway to Long Island. Pack your coziest sweater and some warm fuzzy socks and prepare for an unforgettable and intimate adventure. Embrace the changing colors of the crisp autumn season while sipping on warm cider or an award-winning wine at one of Long Island’s 60 vineyards. Snuggle up next to a fireplace at a charming, historic B&B on the North Fork, or enjoy a spa treatment with a serene view or fresh farm-to-table fare.
Bike through fall foliage and experience the vibrant hues of a fall sunset, explore Shelter Island by kayak, and discover why fall is the best time to visit the Hamptons. Read on to plan the perfect fall retreat on Long Island.
Have a Sip-and-Stay Vineyard Getaway
For Long Island vineyards, fall means that harvest season is in full swing. And with ample vineyards and wineries available to choose from, sipping wine and staying at a nearby B&B or Inn makes for the perfect Long Island fall getaway.
Celebrating over 42 years of winemaking, Pindar Vineyards in Peconic and Port Jefferson is the largest and oldest same family-owned winery on Long Island. Unwind nearby at the Harvest Inn, located right in the heart of North Fork’s wine country with delicious farm-to-table fare and a boutique hotel feel. Stay at the Chalet Inn and Suites with Del Vino Vineyards right next door in historic Northport.
Marcari Vineyards in Mattituck offers a nearly 500-acre vineyard to explore with lodging nearby at the Cedar House on Sound B&B. Rose Hill Vineyards in Mattituck not only has wine tastings and a light bights menu with apple cider donuts but also a beautiful restored, historic farmhouse inn for relaxation and indulgence. Also in the North Fork region is Jamesport Vineyards and the nearby luxurious boutique hotel, Jedediah Hawkins Inn in Riverhead. Sannino Vineyard in Cutchogue is also in the heart of Long Island’s Wine Country and their on-site B&B offers a stunning view of the main estate and vineyards. Get a taste of fall with Sannino’s own Autumn Apple Cider Sangria or check out their “sip ‘n’ snuggle special” which includes a glass of warm spiced wine and cozy Sannino blanket.
Snuggle up Next to These B&B and Inn Fireplaces
Break out the flannels and warm cider – staying at a Long Island B&B or historic inn for a fall getaway is the coziest of cozy fall experiences! Warm up next to the fireplace after spending the day adventuring outside at a nearby farm. Located in East Marion, the Arbor View House has remnants of its original Victorian architecture and is close to many North Fork attractions such as vineyards and farms. Another historic property, the Bellport Inn, invites visitors to experience a relaxed and curated setting just steps from the Great South Bay.
Located on the majestic Peconic Bay, The Shoals is a sanctuary nestled on Southold’s bayside, offering an elemental retreat providing space and calm while you soak in the surroundings. The Shoals is the first of its kind “boatel” that features 20 hotel suites and 20 boat slips. And in downtown Riverhead, the Preston House & Hotel is a 1905 historical home reimagined, offers boutique charm, and makes for an authentic East End getaway.
If it’s fall that means the fireplace is burning at East on Main. A staple in the North Fork community, the fresh, local eatery has all the warm cozy vibes perfect for a fall evening out.
Kick back and relax at American Beech in Greenport and experience the lounge areas and fireplaces in the restaurant area. Its sister hotel, Aqua by American Beech is a newly renovated hotel in Aquebogue with outdoor hot tubs in a majority of their rooms!
Experience Long Island’s Luxurious and Historic Gold Coast
Explore Long Island’s Gold Coast for a look into the elegant and opulent lifestyles of the elite. Resting on the original Guggenheim Estate, Sands Points Preserve was the famed “East Egg” in F. Scott Fitzgerald’s “The Great Gatsby.” Today, the magnificent 216-acre park’s Great Lawn, Rose Garden, Woodland Playground, and forest trails are all open to visitors. Take a tour of the massive 50,000 square foot Tudor style mansion, Hempstead House, or look inside the cliff-side French Norman-style mansion, Falaise.
And in Oyster Bay, visit Planting Fields Arboretum/Coe Hall, a Tudor Revival Mansion where you can view the family’s original furnishings and roam the grounds for a fall foliage experience. Also in Oyster Bay, take a tour of Sagamore Hill National Historic Site, the summer home of Theodore Roosevelt, and explore the nature trail of the 83-acre property. Stay nearby at the Mansion at Glen Cove and don’t forget to take a tour of Westbury House at the Old Westbury Gardens or explore their calendar of events.
Take in the Fall Views, a Stunning Sunset, and US History in Stony Brook Village
Enjoy the sunset while floating through scenic Stony Brook Harbor with Stony Brook Harbor Kayak & Paddleboard Rentals or go leaf peeping at the Avalon Nature Preserve just steps from the harbor. Stay overnight nearby at the Three Village Inn for the ultimate historic village experience and then take a tour of the Stony Brook Grist Mill or the Long Island Museum. And the best part? Stony Brook Village offers a car free experience which means these cozy fall destinations are all within walking distance of each other.
Wander Through Fall Foliage with These Outdoor Activities
Catch the sunset at the Adventure Park at Long Island in Wheatley Heights. After the sunset sets, stay in the trees for their Glow in the Park event where you can zipline through the LED lights for a great fall adventure. Experience yoga’s fundamental link with nature at the Landcraft Garden Foundation where the Giving Room Studio and Juice Bar is hosting outdoor yoga classes throughout the month of October.
For fall leaf peeping, Caumsett State Historic Park Preserve in Lloyd Harbor, Huntington is situated on a scenic peninsula extending into the Long Island Sound and offers hiking and biking trails. For more places to catch Long Island’s fall splendor, take a look at our Insider’s Guide here.
Experience the Tranquility on Shelter Island
Edged in by 11 miles of coastline, Mashomack on Shelter Island is considered one of the richest habitats in the Northeast covering 2,350 acre of interlacing tidal creeks, mature oak woodlands, fields, freshwater marshes, and underwater lands to explore and enjoy.
Bike ride along the winding roads of Shelter Island or visit Sylvester Manor for a Garden & Manor Guided Tour. The 243-acre historic planation and nonprofit educational farm on Shelter Island has trails open 7 days a week from sunrise to sunset. The Chequit is a historic seaside hotel and restaurant perched over the tranquil waters of Shelter Island with a farm-to-table menu that was recently renovated. And the Pridwin Hotel and Cottages is a classic American resort hotel providing guests a unique experience on Shelter Island since 1927 with great dining and a spa offering a full menu of day spa treatments, services, and massages.
Discover Why Fall is the Best Time to Visit the Hamptons
Fall in the Hamptons is a beautiful time of year with so many places to explore and gorgeous places to stay. Beat the crowds and peak season prices and stay overnight like a celebrity at Capri Southampton. For a Hamptons vineyard, look no further than Wolffer Estate in Sagaponack with Baron’s Cove. The hotel and restaurant offer one of the coziest spots for dining in the Hamptons with sweeping harbor views of the Sag Harbor Marina. This luxurious year-round resort offers three wood-burning fireplaces for guests to enjoy.
Stop by for some dinner at the Centro Trattoria & Bar, the ultimate farm-to-fork Italian restaurant in Hampton Bays. With an exquisite outdoor garden foundation and cozy fireplaces, both indoor and outdoor. For more places to stay, the 1770 House in East Hampton has good old-fashioned comforts and modern conveniences including six working fireplaces! And to get that small town feeling, stay at the Southampton Inn, located in the heart of historic Southampton Village and just a few steps from Main Street. Visitors can keep cozy as the weather turns chilly with the Inn’s fireplaces and firepit on the grounds, perfect for toasting marshmallows and sipping hot cocoa.
The Hamptons are also home to the Canoe Place Inn & Cottages with a full-service spa offering exclusive new treatments and a curated collection of clean beauty products. The renovated historic Inn suites are full of character and charm for a cozy weekend getaway on Long Island.