How To Have Your Best Fall Yet

Summer’s finally over (thank God), and now it’s time to kick back and enjoy fall. As an expert in the field (born in October in Upstate New York), I’m here to guide you to your best fall yet.

There’s something magical about fall. I don’t know if it’s the changing colors of the leaves, the fact that adults are allowed to wear costumes, or just the thinness of the air changing the oxygenation of your blood, but the feeling is undeniable. This is the best time of year. 

As someone who has always loved fall, and spent many of those seasons in the best areas of the country to experience fall, I know a thing or two about getting the most mileage possible out of this relatively short season. Buckle up and enjoy the ride.

What to Watch

I’ve got a few standard go-to’s this time of year, but none more important than cramming in all 8 Harry Potter movies between now and Halloween. 

Magic not your thing? Your funeral. But I do have another angle worth considering: the horrors of “back to school.” My picks in this genre: Freaks and Geeks and Napoleon Dynamite. 

Finally, you have to consider more traditional “scary” movies here as well. As a former homeschooler who grew up watching AMC and TMC (back when all they showed were classics), I have a particular fondness for older movies in this space: Frankenstein, House of Wax, The Wolf Man, etc. Find something that stars Lon Chaney or Boris Karloff, and you’re in for a good time. 

What to Do

You can’t just watch TV. Fall is also the perfect time to get back outdoors after a brutally hot summer. Now again, I’m from New York, so it’s hard not to make some highly-regional suggestions here. Some of the prime fall experiences just fall a little bit short in Tennessee and other non-North Eastern states. 

Go to a pumpkin patch or nursery

Don’t settle for some rinky dink grocery store pumpkin (or more worse yet, an artificial one). Go find a place out in the country where you can pick your own big, hefty pumpkin that you need to pull to your car on a wagon. 

Bonus points if you carve this pumpkin into a jack-o-lantern. Pro tip if you do: don’t get one of those weak, baby pumpkin carving kits. Pull out a kitchen knife and a ladle, and start stabbing away. Will you cut yourself? Of course you will. But those scars will serve to remind you of the incredible fall you had way back in 2023. 

Go apple picking

This is a hard one in much of the South, but it’s a BIG deal where I’m from. Honestly, it’s worth a trip up to the North East to experience the wonder of picking your own unbelievably fresh, delicious apples while also taking a hayride around the orchard and downing a few apple spice donuts. 

Leaf peep on the Kancamagus

If you’re already in NY picking apples, drive a few hours into New Hampshire for some of the most mind-blowing colors you’ve ever encountered. The Kancamagus scenic byway is a 34 mile path through the White Mountains that will leave you speechless.


Look, people who don’t participate in trick or treating are jerks. If you have a kid or two, you have the perfect excuse to get out there in a costume yourself. Don’t be the goof walking along in regular clothes. 

Don’t have kids? Then you had better freaking get some candy and leave your porch light on. No one likes a Scrooge this far before Christmas. Want to really wow your neighbors? Be the superstars who hand out full-sized candy bars. 

What to Wear

On Halloween, a costume – and don’t you dare forget that. But what about your day-to-day look? How do you avoid looking like a complete dork while at the pumpkin patch or exploring New England? Don’t worry, I’ve got you covered:


Search your feelings, and you already know the answer: Bean Boots. Quit overthinking and pull out your credit card. New boots always put some pep in your step.


Fall is weird – it’s too warm for a full blown jacket, but it still gets a little nippy. You need a nice, thick hoodie or a shawl-collar cardigan (if you’re feeling fancy). 


You can get away with chambray, but this is flannel season first and foremost. Don’t waste your time with those horrible micro plaids, get a nice, big, bold pattern that reminds you of why you’re here in the first place: to squeeze the ever-living lifeblood out of fall. 


It’s denim weather, and it’s time to explore some super thick Japanese selvedge. Don’t you want a little extra knee protection when you’re inspecting that massive pumpkin you’re about to buy?

I know that 21 ounces is intimidating, but I’ve been wearing these for years. Give them a month of consistent wear, and they’ll feel like sweatpants in no time. 


This one’s a no-brainer

What to drink

I’ll admit: I think alcohol is pretty gross on the whole. I’m sure there’s some great fall cocktail out there, but here are some teetotalist solutions:

Seasonal coffee shop offerings 

Now’s the time to experiment with what your local coffee shop is coming up with. Don’t ask for any changes, just take it as it comes and see what you like best. 

Too scared of what the barista’s slinging? Head to Starbucks, and you’ll know what to do

Apple cider

I’m a big cider fan – hot or cold, spiced or plain. Get it while the getting’s good. 

Now, you can totally get it at your favorite grocery store, but I’d suggest steeping in the fall feelings a bit more by picking up a gallon at the farmer’s market or at a local farm. Grab some local honey while you’re at it, and stir a little in when you’re feeling daring. 

Root Beer

The only beer I like. In fact, when I was a little kid, I was terrified that I would become an alcoholic if real beer tasted like root beer. Fortunately for me, I’m 36 years sober thanks to the fact real beer is so much worse than the root variety. 

Not sure what to get? I’m partial to IBC and Virgils (there’s just something about a glass bottle), but A&W isn’t half bad either. 

So there you have it: a list of activities and items guaranteed to kick your fall up a notch. Take the rest of September to get your plan in place so you can hit the ground running October 1st. Go forth!

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