
It’s exactly one week after Labor Day and if you’re anything like me, you’re probably wallowing in a deep puddle of post-summer blues. Your weekend plans are dwindling, your pockets are nearly empty, your tanned skin is already fading and you’re not ready to bid your last goodbyes to your beloved warm weather.
Well, in the middle of floundering in my irrational self-pity, I realized something. Transitioning out of a intricately planned, sunny summer doesn’t have to be a complete buzz-kill.
Fall happens to be a great time to to be on Long Island, the place I’m fortunate enough to call home! Even if you’re not too familiar with Long Island, you’ve most likely heard of “The Hamptons” some time in passing, the summer stomping ground of New York’s rich and famous. The Hamptons are located on the south shore of the island and while they definitely rule the summer months, the North Fork of LI happily claims autumn.

In the tristate area and looking for an autumn excursion? Every fall millions of visitors make their way east, to my hometown and beyond, hoping to take advantage of Long Island’s rich rural culture. There’s no shortage of things to do and plenty of fun fall festivities to choose from!
Plan a visit to the North Fork Wine Trail
While most wineries on Long Island are open year round, fall may just be the perfect time to make the trip. Why? It’s harvest season! Long Island’s North Fork is known as “Long Island Wine Country” and is home to over 30 wineries and 3,000 acres of planted vineyards, many of which hold fall festivals celebrating the fruits of their labor!
Sprawled out very neatly along two main roads called the “North Fork Wine Trail,” these inviting humble wineries are hard to miss. Taste the very best of Long Island wine and meet the families behind the business while gazing out over grapevines stretching as far as the eye can see!
Learn more about Long Island wines. 
Spoil yourself at Briemere Farms
Briemere Farms, located right on Long Island’s own Sound Avenue is reason enough to make a trip out to the North Fork. This historic fruit farm has become a go-to among locals and vacationers, not only for their delectable fresh produce, but also for their homemade pies, muffins, cookies, cakes and jams.
Each and every tasty marvel is prepared from scratch with homegrown ingredients right on the very farm grounds. It truly is a little slice of all-American heaven. You’re sure to encounter an ample crowd spilling out the door, but don’t you dare let that turn you away. One bite of a heavenly Briemere’s raspberry cream pie and you may actually begin to reevaluate the meaning of life itself. 

Pick your own produce
Bordered by water on all sides, the North Fork’s high water to land ratio make it one of the leading growing locations in the world! While the dead of summer may be the best time to harvest some local produce on Long Island, autumn brings a whole new array of crops to the court.
Farm stands all over the North Fork proudly display their bounty hoping to draw in customers to ravish their alluring, juicy supply. U-pick areas line the main streets offering visitors a chance to take part in the agricultural experience by venturing into the farm fields and hand-picking their very own perfectly ripe apples and pumpkins!
What you’ll find fresh at the farm stands this fall: Apples, Blueberries, Broccoli, Cabbage, Cauliflower, Corn, Cucumbers, Eggplant, Lettuce, Peaches, Pears, Peppers, Plums, Potatoes, Pumpkins, Spinach, Squash and Tomatoes!
Click here for an interactive map of Long Islands Farm Stands.
My favorite place to go apple picking: Harbes Farm

Hit up a Halloween Haven
I hate to admit it, but summer has come and gone and October is just around the corner. Still that means everyone’s favorite creepy, crawly holiday is near! But don’t worry, you won’t have to wait until the 31st to embrace your spooky spirit on Long Island, as NOFO is just the place to make the most of this fright fest.
All October long, city dwellers of all ages flock east in search of the perfect plump pumpkin and to indulge in a glass of rich spiced apple cider. The activities are endless from hayrides, corn mazes and parades to haunted houses, themed events and costumes masquerades!
Just to name a few of my favorites:
Darkside Haunted House. Calverton, NY.
Harbes Robbin Hood themed Corn Maze [day] and Spooky Maze [night]
Edgar Allen Poe Festival. Riverhead NY. 
Get your Golf on
The summer heat is finally starting to die down making it the ideal time to break out your clubs and head to the links. With many courses open through December, you’re likely to enjoy a less crowded course and affordable tee times without melting under the summer sun. While some courses on the North Fork are so exclusive that you won’t even see a sign as you pass, there are plenty of picturesque public courses to choose from, many offering waterfront vistas.
For more information on Long Island courses head here.
Enjoy a Sunset Dinner
Many Long Islanders seem to believe that autumn is the best time to catch an exceptionally special island sunset. With nearly 40 miles of beachy coastline to choose from, it shouldn’t be difficult to find the perfect spot to watch the sun splash into the Long Island Sound. Pack a picnic or choose from one of many phenomenal waterfront restaurants and simply gaze in amazement at the bleeding hues of the fiery sun fading over the horizon.
Two of my favorite waterfront spots:
Claudio’s. Greenport, NY. Website.
Pace’s Dockside. Mattituck, NY. Website. 
Live Music and Tribute Bands
New York City may be the heart of the NY music scene, but more and more the North Fork is putting its name on the map. Not only is the area known for hosting small-scale festivals and tribute bands, but it has also begun attracting big names in the industry. Venues such as Martha Clara Vineyards have hosted headliners Avicii, Pharrell Williams, Keith Urban, Duran Duran and more.
Not into the cramped concert scene? Many restaurants, breweries and vineyards continue live music into the fall with tribute bands covering music by iconic groups such as U2, Journey and even the Beatles.
Keep on the lookout for upcoming events on eventbrite and at venues like Martha Clara Vineyards and you never know what you’ll find!

Hope to see you soon!! 😀
Do you have any fun activities planned for fall?




That all looks so great! We tend to forget what we have at hand when planning and enjoying all the long distance trips. And I love autumn, with all its colours. If only it could still be a little bit warmer 😉 Congrats on being the new co-host 🙂
I knew that the Hamptons was a huge spot to visit during the summer, but I didn’t realize that there was so much to do North Fork and Long Island during the fall! You pretty much had me at wineries, and visiting one during the harvest would be such a fun experience!
it looks so pretty there, I like the way you made this into a sort of bucket list for whoever visits North Fork in the fall!
Totally gorgeous and a great place to spend autumn – these are such great picks!! 🙂 The sunsets and the great fresh produce look like heaven to me!
Wow- this is a very comprehensive post! I love pumpkins and all, but the wine trail made my ears perk up 🙂
Looks like the perfect place to spend Autumn! Though I hate that summer is almost over, there is something refreshing about the fall.
Gosh I love a live band and a cold drink…and that sunset looks amazing! Glad I found your post on Travel Tuesday…looks like this was an amazing place!
I would be definitely hitting up the wineries and picking my own produce. What an adorable part of the US!
Oh come on! You’re so lucky you live on Long Island!!! 🙂 I guess with all the stuff around and New York just around the corner, you never get bored :)))). BTW – I love wine trails and wine tasting :)))
I invite you to check out my VIDEO REPORT from my short visit in TOKYO
http://www.travelekspert.com/2015/09/tokyo-experience-movie.html