Happy Fall, Y’all! I couldn’t be more excited about Pumpkin Spice Everything, a fashion show of every scarf I’ve ever owned, and my doorman staggering under the weight of my new boot packages. If you’re like me, you’re excited to ditch sweaty t-shirts and shoes that need to be worn without socks. My sweaters are too cute to be eaten away by moths in my mom’s basement for another month; catch me in 75 degree weather wearing all of my light jackets at once. While there are plenty of great spots in Manhattan to show off your Fall Lewks, it’s more fun to show up for the gram in your perfectly cuffed jeans and light jackets with something in the background other than a pile of garbage on the sidewalk that you can smell through the picture. Fortunately, the best places to be as the leaves are changing are all within driving distance of our not always cozy city. Make friends with someone who keeps a car in the city (or perhaps at their parents’ house on Long Island) and hit up these beautiful locations. Or take advantage of the Long Island Railroad, Metro North, Amtrak, and the Jitney. You might even want to take a Friday off (since sadly, summer hours are over).
Nyack, NY
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Nyack is a beautiful town an easy hour drive from New York City. Stay at gorgeous The Time Nyack and, if you can bring yourself to leave the grounds, explore farmers markets, beaches, the historic Edward Hopper House, or charter a sailboat to cruise the Hudson River. I can’t imagine a better photo op than sipping champagne on a yacht with the dazzling city skyline behind you and your date.
Mattituck, Long Island
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The North Fork of Long Island is a beautiful destination all year ‘round, but the Fall is when the towns come to life with bountiful harvests of vegetables, pumpkins, hay rides, and WINE! Shinn Estate Farm House is a cute bed & breakfast surrounded by acres of vineyard that you can stroll with bae as you sip your morning coffee. Don’t miss the chance to explore nearby vineyards during the day to get a taste of delicious regional wines. There are also great selections of produce and fall fare from local farms such as Krupski’s. Stroll Love Lane if you’re looking for shops and treats!
Cherry Grove, Fire Island
Are you gay and in the New York City area? Great, see you at Cherry Grove! Fall does not mean the end of festivities on Fire Island. In fact, Cherry’s On The Bay has a Halloween party hosted by DJ Queen Levine. Take the ferry from Sayville and try not to fall in the Great South Bay after partying all night at Cherry’s!
Babylon, Long Island
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All within walking distance of the Long Island Railroad after a quick 1.5 hour trip from Penn Station or Atlantic Terminal you can find adorable shops, great brunch places, nail salons, tanning, and the most delicious margaritas and tacos. You can also take a walk in Argyle Park and observe some local fauna and flora, but watch out for geese poop. Babylon is a town that is fun for the whole family and really lends itself to day tripping from the city. I like to seamlessly transition from brunch to before-dinner drinks with sushi, to margaritas and tacos at Swell Taco, and then head on over to the Post Office for an energetic evening.
Philadephia, PA
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Did you know the Philadelphia area is home to some of the nation’s oldest and most beautiful botanical gardens and arboretums? In fact, America’s oldest garden, Bartram’s Garden, is just minutes away from The Liberty Bell. If you’re interested in America’s history, this is a great location. Show off that history degree to Bae and smooch under the loving eyes of our founding fathers. On the other hand, you can visit Eastern State Penitentiary for a day tour and cuddle up while you pretend to be brave.
New Hope, PA
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I know your Tinder bio claims that you love the outdoors, this is your chance to go once for the year and snag a pic with a tree! Washington Crossing Historical Park is an outdoor gem ideal for walking in nature and walking in the shoes of George Washington. If nature trails aren’t your speed, check out the Wine Trail, Ale Trail, or the Distillery tour. Host to a plentiful assortment of bed and breakfasts, you can find great shopping, dining, and impressive theater in this lovely town located just hours outside of New York. Take the bus to Lambertville, NJ for easy access!
East Lyme, CT
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I bet you were wondering when we were going to bring up the conveniently located neighbor across the Sound, Connecticut. While I’m sure the whole state is lovely, I recommend checking out East Lyme for their mile long Boardwalk, Oyster Festival, and limitless nature walks. Nehantic State Forest and Rocky Neck State Park are both a few hours drive from New York. You’ll want to stay for the weekend so you can check out their museums, local restaurants, and breweries!
Shelter Island, Long Island
Do you love the North Fork and the South Fork of Long Island and sometimes can’t choose where you want to spend time? I have the perfect solution for you! Shelter Island can be easily reached via a short Ferry ride from either side of the island. Travel in your car to get to your destination on the island easily or as a solo passenger. There are delicious restaurants with fresh sea food right on the water such as Salt. The Mashomack Preserve has great hiking trails as it covers about one third of the island. Trails as short as 1 mile or as long as 10 miles will offer you a peaceful chance to get away from the hustle and bustle of city life.
Southampton, Long Island
I love Long Island and can’t overstate the beauty that’s right outside our doors if we are only brave enough to take the Long Island Railroad. Make sure to check out the Jitney option as well when heading to the forks! Southhampton is known for great shopping and even better beaches. Check out the Riverhead Aquarium for a day of education and aquatics!
Hudson, NY
Endearingly termed Upstate’s Downtown, you’ll find countless locations to make memories with Bae in Hudson, New York. Take a GPS guided walking tour and learn all there is to know about the town’s cemeteries, firehouses, churches, and more! The best part? They’re totally free! There are bed and breakfasts to choose from so stay the night and see the sights!
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