I made a promise to myself this year: take advantage of those three-day weekends by enjoying the great outdoors instead of sleeping in till the PM hours. Those instances where I get an extended break from work are rare, so I’ve made it my mission to fill those off days with memorable activities.
ChatGPT has sent me all over New York this year since I’ve begun using it as one of my digital curators for fun activities I may not have known about before. My trip-planning chatbot has made me aware of local museums, restaurants, bookshops and even a few oddities that I’ll be sure to bring my buddies to the next time around.
For my next “fun-time excursion planning” session with ChatGPT, I gave it a new challenge: “I only have $100. Plan a perfect fall weekend with the most fun and affordable activities for me in New York City, with that in mind.”
Not only did ChatGPT lay out affordable ways to enjoy each day, but it also exposed me to an activity that made me realize I’d been missing a nostalgic element from my childhood.
Friday’s festivities
ChatGPT laid out a plan for all three days alongside an approximate budget for all the activities it suggested for each one.
Friday’s plan included a free museum, a fall evening walk and a cheap dinner to cap the night off that came out to $18. Out of those three fun proposals, the one that caught my attention the most was the free night of culture I could experience at the MoMA (The Museum of Modern Art): If you're a New York State resident, UNIQLO Friday Nights gives you free admission to MoMA from 5:30–8:30 p.m. You need to reserve a ticket in advance. That immediately gives you a $30-ish museum experience for $0.
I made sure to add that museum crawl to my Friday schedule so I knew exactly what I’d be doing after logging off from work.
Saturday’s pursuits
For the official start of the weekend, ChatGPT recommended a cost-effective hangout that started in Brooklyn and included a free festival, a quick bite to enjoy and a sunset walk that would definitely put my mind at ease.
The price for this plan came to $35, which is still cheap enough to leave me with enough funds for the third and final day. ChatGPT’s lineup of events that won’t break the bank definitely appealed to my curiosity and taste buds — these three picks got added to my three-day leisure list:
- ALIVE NYC by Daybreaker is happening Saturday at Brooklyn Bridge Park, running 6 a.m.–8 p.m., and is free with RSVP.
- Or head into Bed-Stuy for the African Restaurant Week Festival, which is also free and runs Friday–Sunday.
- Head toward Fort Greene, where Kréol Fest 2026 is also happening this weekend and is free with RSVP. You could easily spend several hours wandering, listening to music and checking out neighborhoods without spending anything.
ALIVE NYC’s promise of live music, a gathering of friendly people, interesting guests and chill vibes gave me something to look forward to. The African Restaurant Week Festival also stood out as a worthwhile option worth considering since shopping, eating and dancing among a large crowd of like-minded people is right up my alley. The Kréol Fest offered the same three bullet points of amusing diversions, but with a Kréol-focused twist.
Sunday’s entertainment
With Sunday in mind, ChatGPT combined the cost of its main plan (which is $30) and the one it set aside for backup purchases (which totaled $17), which hit my limit of $100. The main plan focused on trekking through Central Park, enjoying yet another free festival and stuffing my face with some cheap comfort food.
ChatGPT’s suggestion for an afternoon activity sparked my interest the most, as it appealed to my young soul in need of something that evoked grade school field trips:
- This is the wonderfully weird part. The NYC Fungus Festival is happening Sunday at The Battery from 11 a.m.–4 p.m., and admission is free. So you could do Central Park in the morning, wander downtown and finish with a completely unexpected mushroom festival.
When I did my research on the NYC Fungus Festival, it made me realize that I’d been missing out on the sort of fun that I’d implore my parents to sign off on when my school wanted to take my class out for some intriguing endeavors.
Heading to The Battery in Lower Manhattan to study different kinds of mushrooms, participate in discussions about them, go on nature walks to find more, sit in on workshops, enjoy the work of local artists, munch on some grub from food vendors and attend a Fungi Fashion Parade sounds like an awesome plan. I’m sure I’ll feel like a 10-year-old again as I bask in the wonder of fungi on the final day of my last three-day tour around my city.
The takeaway
ChatGPT’s final statement about my three-day escapades was a bit humorous yet still informative:
Don't pay for anything that NYC gives you for free. This weekend, you've got free museums, parks, festivals, outdoor concerts/events, neighborhood walks, waterfront views and an enormous city to explore. NYC's Department of Cultural Affairs maintains an extensive list of free and pay-what-you-wish cultural institutions.
Heading to the MoMA on Friday night, taking the train to Bed-Stuy for the African Restaurant Week Festival and bringing my fun to an end on Sunday by attending the NYC Fungus Festival helped me set my three-day weekend plans in motion.
Doing all of those activities without having to worry about going over $100 helped me rediscover my love for activities that evoked a school field trip. So, not only did I save money, but it helped rekindle my youth.
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