Spectacular summertime escapes may be what Long Island is best known for, but many will argue that fall’s crisp days are the best time of year to explore the region – home to hundreds of pick-your-own farms, haunted historic sites, an award-winning wine country, wondrous fall foliage, extravagant Halloween-themed events and much more. That’s why we rounded up 11 bucket list worthy Long Island experiences that are easily accessible by the Long Island Rail Road and sure to provide a seamless and memorable fall adventure for all.
1. Revel in the East Coast’s Largest Waterfront and Oyster Festival
The Oyster Bay Oyster Festival has a long tradition as the East Coast’s largest waterfront oyster festival featuring live entertainment, incredible ships, top-notch artisans, pirate shows, midway rides, and the iconic oyster eating and shucking contest. On October 15th and 16th, visitors can attend the annual celebration for themselves and check out the food court where unique oyster, clam, and other seafood options are served.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at the East Norwich Inn, The Mansion at Glenn Cove, or the Inn at Fox Hollow
HOW TO GET THERE: Take the train from Penn Station to Oyster Bay. The train stop is conveniently located at the entrance to the festival. LIRR will be running more trains on the Oyster Bay Branch to get you there. For those coming from Suffolk County, free shuttle buses are available from the Syosset station on the Port Jefferson Branch.
LIRR2. Experience the Immersive Hocus Pocus-Themed Pop Up Bar “Witch Craft”
The “Witch Craft” Halloween pop-up bar is a must-see live performance and immersive dining experience. Located in Farmingdale on select dates in October and November, the menu will include witchcraft-themed cocktails and mocktails with props and decorations from the Hocus Pocus movie. An immersive experience for Hocus Pocus fans and foodies alike, the pop-up bar is one you don’t want to miss, and it’s just a few steps away from the LIRR!
Want a sneak peak? Check out this episode of Discover Long Island's Long Island TV, Just a Bunch of Hocus Pocus in Farmingdale:
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at the Homewood Suites by Hilton Long Island - Melville, the Hilton Garden Inn Melville, or the Courtyard by Marriott Republic Airport Long Island / Farmingdale
HOW TO GET HERE: Take the train from Penn Station to Farmingdale, then walk to the pop-up bar.
3. Harvest Season! Pick Your Own Apples, Pumpkins, Corn, and More at Dozens of Family-Owned Farms
It’s no secret that Long Island has some of the most diverse and gorgeous farms with picturesque flower fields, fresh fruits, and vegetables. Whether you’re looking for a place to pick your own apples, pumpkins or just kick back and enjoy some cider, Long Island’s farms are a fall attraction that you don’t want to miss out on this fall.
Fall in love with Harbes Farm & Vineyard located in the heart of Long Island’s North Fork. The 100-acre Mattituck-based farm has a popular barnyard and farmstand with farm-fresh produce including their signature apple cider donuts, pumpkins, and corn maze. And in Manorville, Waterdrinker Family Farm’s Fall Festival has hayrides, a corn maze, and pumpkin picking!
OVERNIGHT STAY OPTION: Make it a weekend getaway by taking advantage of the MTA Away Deal to Hotel Indigo Long Island - East End (close to Waterdrinker), or stay at The Preston House (close to both), the Cedar House on Sound B&B (Mattituck), or the Shoals (close to Mattituck).
HOW TO GET HERE: Take the train from Penn Station to Mattituck or Riverhead. The MTA Away Deal includes round-trip transfers to Hotel Indigo, or hop in a rideshare to get to your hotel or farm.
4. Two Words: Wine Country
Known as Long Island’s wine country, the North Fork’s fall harvest season provides ample opportunities for wine tastings and wine tours. For a care-free, car-free day trip, join the LIRR’s Escorted Wine Country Tour on October 29, and leave the driving to us! For an on-your-own visit, Jamesport Vineyards’ great lawn is the perfect setting for enjoying great wine and light fare. Stop by RGNY’s tasting room in Riverhead to learn how to taste and pair wine like a pro or take an educational wine class at Terra Vite Winery & Vineyard. Sip renowned wine at Palmer Vineyards, visit the campus at Lenz Winery, or glimpse the unparalleled view of the Long Island Sound at Kontokosta Winery’s waterfront location.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at Stirling House Waterfront Inn, Cedar House on Sound B&B, Jedediah Hawkins Inn, Arbor View House B&B, the Shoals, American Beech, or the Sound View.
HOW TO GET THERE: Meet us on the train for LIRR’s Escorted Wine Country Tour or take the Ronkonkoma branch to Long Island’s Wine Country at Riverhead, Mattituck, Southold, and Greenport. No matter where you hop on or hop off, you’ll be no more than a 5–10-minute drive or bike ride from several award-wining wineries.
5. Small Town Splendor with Fall Traditions and Festivals
There’s nothing better than a small-town festival where the community comes together to celebrate anything from old-time traditions to music to fall.
The Montauk Chamber of Commerce and Visitors Center is hosting their annual Montauk Fall Festival on October 8, with live bands, pumpkin painting, kids crafts, bouncy rides, and a food tent! Take the LIRR’s Montauk Lighthouse Escorted Tour to the lighthouse and festival, and leave the driving to us! And in Stony Brook, the Ward Melville Heritage Organization presents the 32nd annual Stony Brook Village Halloween Festival on October 31. The festival will have trick or treat in the shops and a scarecrow competition. Further out east, downtown Riverhead has their annual Halloween Fest on October 22 with coffin races, trick or treat along Main Street, and a costume/float parade.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at Gurney's Montauk Resort & Seawater Spa, Marram, Montauk Manor (Montauk), Three Village Inn (Stony Brook), Hotel Indigo East End or The Preston House & Hotel (Riverhead).
HOW TO GET THERE: Meet us on the train for the Montauk Lighthouse Escorted Tour, or take the train from Penn Station to Montauk, Stony Brook or Riverhead. From there, the Montauk, Stony Brook, and Riverhead Festivals are within walking distance, or you can call for a cab to get there.
6. Experience Autumn from New Heights with Stories-High Adventure Courses
Adventure amongst the fall foliage or visit the park at night for “Glow in the Park” – Adventure Park’s signature nighttime event. Visitors can zipline and climb through an illuminated forest to high energy music with different unique themes. As the area’s largest zipline and climbing adventure experience, fall is a great time to experience the changing colors at eye level.
Take advantage of the thinner crowds and milder temperatures that the fall has to offer and have an adventure up in the sky at Jones Beach with WildPlay. Featuring a ropes course on an elevated platform, a challenge course, a child-friendly course, and a zipline, no trip to one of Long Island’s most popular beaches is complete without a stop at this daredevil experience. Discover Long Island's Long Island TV visited and had a wildly good time! Take a look before you go.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at Allegria Hotel or The Freeport Inn and Marina (near WildPlay), Hilton Long Island/Huntington or Four Points by Sheraton Melville (near the Adventure Park).
HOW TO GET THERE: Take the train from Penn Station to Long Beach (steps away from the Allegria Hotel), Freeport, or Wyandanch (close to the Adventure Park).
7. Brave a Haunted Historic Site and Ghost Hunt with Paranormal Experts
Made up of a dozen historical buildings, the Southampton History Museum has two of the most haunted places on Long Island: the Rogers Mansion and the Halsey House. Here, guests and employees have documented unexplained footsteps, items being thrown across the basement, and shadowy figures following people through the house. The activity is so widespread and regular that Long Island Paranormal Investigators have set up a permanent residency here offering ghost tours once a month throughout the year.
For dinner at a historically haunted site, Stony Brook Village has the place to visit. Originally built as a farmhouse in 1710, the village’s Country House Restaurant is haunted by the spirit of a woman named Annette Williamson who was murdered after she welcomed British soldiers into her family home during the Revolutionary War. Restaurant visitors say that they hear her cries, see light bulbs flashing, and hear footsteps running and walking. To learn more about Stony Brook Village’s haunted past, the Stony Brook Village Walking Ghost Tour, “Secrets & Spirits,” allows participants search for spirits through time with new stories of local hauntings along Stony Brook’s coastal community. Ghost stories include the Long Island witch trials and the woman in white at the Stony Brook Grist Mill.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at The Estate at Three Village Inn, Hilton Garden Inn Stony Brook, or The Capri Southampton.
HOW TO GET HERE: Take the train from Penn Station to Stony Brook or Southampton. From there, grab a rideshare to your haunted historic site or hotel. If coming from the Stony Brook train station, you can walk to the village center.
8. Immerse Yourself in Long Island’s Fall Splendor with Leaf Peeping, Hiking and Biking Trails
With hundreds of parks and preserves, Long Island is a haven for outdoor and nature enthusiasts. Planting Fields is a magnificent Gold Coast estate from the 1920s in Oyster Bay that is perfect to roam and take in the imagery this fall.Featuring 409 acres of greenhouses, rolling lawns, formal gardens, woodland paths, and an outstanding plant collection, Planting Fields’ picturesque views are a must see this fall.
Likewise, with over 50 miles of hiking, horseback riding, nature trails, and fishing, the Connetquot River State Park and preserve has over 3,000 acres of land and water perfect for scenic fall excursions. And along the same river, the Bayard Cutting Arboretum in Oakdale has 690 acres of lawns and open meadows, a wildflower garden, a marshy refuge, and many nature trails for bird watching. Serving as an oasis of beauty and quiet, the arboretum is a source of pleasure, rest, and refreshment.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at Mansion at Glenn Cove, or the Inn at Fox Hollow.
HOW TO GET THERE:Take the train from Penn Station to Oyster Bay or Oakdale. Then grab a rideshare or call a cab to get to your hotel or leaf peeping trail.
9. The Long Island Monster Gallery has Spooky and Realistic Renditions of Life Size Monster Replicas
The Monster Gallery in Mineola is Long Island’s first gallery dedicated to horror and Halloween cinema comes to life again for a fall season of monsters, madmen, and mysterious creatures. Featuring two floors, the gallery showcases over 30 life-size movie monsters accompanied by theatrical sets, lighting, and soundtracks. Each monster has been meticulously hand-crafted by artists from around the globe.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying SpringHill Suites by Marriott Carle Place Garden City or the Garden City Hotel.
HOW TO GET THERE: Take the train from Penn Station to East Williston train station, where the Monster Gallery is within walking distance.
10. Fall in Love with the North Fork’s Historic Charm, Farmlands and Festivals – Including Century Old B&Bs, Antique Shops, Nature Trails and More
Known for its rich farmland and award-winning vineyards, the North Fork of Long Island is the perfect place to fall in love with a cozy B&B escape. Whether you are looking to snuggle up next to a luxurious fireplace, explore a nature trail or antique shop, or sip quality wines at the nearest vineyard, the North Fork will make your autumn dreams a reality! Peruse North Fork boutiques and antique shops including North Found and Southold’s Lost & Found.
Find one-of-a-kind homes to rent with New York Rental by Owner or explore the range of unique boutique accommodations throughout the region.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at Stirling House Waterfront Inn, Cedar House on Sound B&B, Jedediah Hawkins Inn, Arbor View House B&B, the Shoals, American Beech, or the Sound View.
HOW TO GET HERE: The LIRR’s Greenport branch on the Ronkonkoma line has four stops in the North Fork including Riverhead, Mattituck, Southold, and Greenport.
11. Hit the Casino
Long Island’s fall entertainment is not just limited to farms and fall foliage. Jake’s 58 Casino Hotel offers a state-of-the-art gaming facility featuring two floors of electrifying gaming action and all the pulse-pounding games you love. They have slot machines, electronic table games, off track betting, and so much more.
OVERNIGHT STAY OPTION: For a seamless, car-free experience, stay on-property at Jake’s 58 Casino Hotel.
HOW TO GET THERE: Take the train from Penn Station to Ronkonkoma. From there, schedule a rideshare app service or grab a cab to Jake’s 58.
