Issue 03: Back Outside, and Back Together

There are certain weekends that remind you exactly why you love living here. For me, almost all of those weekends are in the fall (also because I loooooove a good cardigan).

The weather finally cools enough to swap iced coffee for something warm. The leaves begin to hint at the colors to come. Farm stands fill with pumpkins and fresh cider, families head to local orchards, and every calendar seems to have another festival circled in red. We’re so lucky in Westchester to have an intersection of all of these things right in our backyard. Fall has a way of bringing us back outside—and, perhaps more importantly, back together.

That spirit of community is something we wanted to celebrate in this issue.

One event that perfectly captures it is Yonkers Riverfest, returning to the waterfront this month. Every year, thousands of people make their way downtown not just for the music or the food, but for the experience of sharing a day with neighbors, discovering local businesses, and celebrating everything that makes Yonkers such a vibrant city.

This year's entertainment lineup raises the bar even higher. From the theatrical energy of The Lady Gaga Experience featuring Haus of Monsters to a freestyle-filled evening with DJ Frankie Cutlass and Lisa Lisa, the festival promises something for every generation. It's the kind of lineup that gets parents reminiscing, kids dancing, and everyone grooving the night away along the Hudson River.

Riverfest is also a reminder of what makes local events so important. They give artists a stage. They introduce us to businesses we've never visited. They bring families into downtowns that continue to grow and evolve. They create the kind of memories that become traditions.

Throughout this issue, you'll find plenty of ways to embrace the season—from guides to fall festivals and local events to the best places for seasonal coffee, weekend adventures, and hidden gems worth exploring. And I invite you to send us your missed connections, if any. We are trying to be a little more analog in a digital world and what’s the root of that? Human connection.

Here's to crisp mornings, colorful afternoons, and a fall filled with new adventures.

See you out there,

Cristiana Caruso
Editor, Not Upstate

Here are some of the best events worth leaving the house for.

Hispanic Heritage Month Featured Artist: Breana Ferreira
Clay Art Center, Port Chester
Hispanic Heritage Month exhibition featuring ceramic artist Breana Ferreira.

San Gennaro Feast of Yorktown
One of northern Westchester's favorite annual festivals featuring Italian food, carnival rides, live entertainment, vendors, games, and that cozy Italian hospitality.

Dionne Warwick – “Over and Out” Farewell Tour
Paramount Hudson Valley Theater, Peekskill
The final tour from the legendary singer is making a stop right here in Westchester, so make sure you’re there for this special moment in music history.

Emo Idol - Live Band Karaoke
Yonkers Brewing Co., Yonkers
Live band, Shakeout, will be playing "The Black Parade" by My Chemical Romance, and then the audience can sign up to sing a song with the band from a list of over 50 emo night classics. Tickets are $15 in advance and $20 at the door.

The Great Jack O'Lantern Blaze Opens
Van Cortlandt Manor, Croton-on-Hudson
One of the Hudson Valley's signature fall attractions featuring thousands of hand-carved illuminated pumpkins, a spooky tavern, and will leave you in the . The event runs through early November but has been known to sell out

Mystic Moon
Harvest Moon Farm & Orchard, North Salem
Evening fall festival with apple picking, food, live music, pumpkins, and seasonal activities.
Runs weekends through November.

Legendary Tours Begin
Washington Irving's Sunnyside, Irvington
Ghost stories and folklore inspired by Washington Irving, told in his former (or current, we don’t know who is still lurking around..) home. Runs through November.

Fall Crafts Show
Lyndhurst Mansion, Tarrytown
This seasonal artisan market features handcrafted goods, local makers, and the most unique items to decorate your house with. Runs from September 18–20.

An Evening with John Cusack
Paramount Hudson Valley Theater, Peekskill, 8PM
Join the legendary actor for a screening of Say Anything followed by a Q&A session. Limited meet and greet tickets are available, boomboxes not included.

Yonkers Riverfest
Downtown Yonkers Waterfront, 12PM-7PM
One of Westchester's biggest community festivals featuring live music, food trucks, family entertainment, and more. Scroll down for more details on the event, including the closing acts that you’re not going to want to miss.

75th Annual Herb Fair & Market
Caramoor, Katonah, 10AM-4PM
This free event on Caramoor’s sprawling grounds brings together garden vendors, herbs, plants, crafts, demonstrations, and local nosh. Who says no?

The Capitol Theatre 100th Anniversary Celebration
Port Chester
The Cap is celebrating a century of iconic performances in a way only the Cap can: by throwing a banger. Pink Talking Fish is headlining the night and will perform a show honoring the legendary artists who have rocked the venue over the years, featuring special guests and surprise moments throughout the night.

Sleepy Hollow Street Fair
Sleepy Hollow
One of the largest street fairs in the Hudson Valley is back for another year, with the streets packed to the brim of crafts, vendors, live entertainment, and all things spooky. I’m going to hold your hand when I say this–take the train. Parking is going to be wild and the traffic leaving is scarier than anything Washington Irving could write.

JazzFest White Plains
Multiple Locations in Downtown White Plains
Five days of jazz performances at venues throughout downtown featuring nationally recognized artists and local musicians. Event runs from September 23-27.

Westchester Comedy Club
Rye Bar & Grill, Rye, 7PM
Stand-up comedy night featuring touring comedians. If you miss it this go around, the show is also running October 22 and November 12.

The American Popular Songbook
Reid Castle, Manhattanville University, Purchase, 7PM
A must-see for music lovers, the evening will come alive with a lively performance by renowned jazz musician Mark Morganelli & The Jazz Forum All-Stars. The group will play a wide-ranging selection of cherished compositions by celebrated American composers like Richard Rodgers, George and Ira Gershwin, and Duke Ellington.

Myths & Mysteries of the Octagon House
The Armour-Stiner Octagon House, Irvington
To get really into the Halloween spirit, take a historic ghost tour exploring local legends and architecture at this National Historic Landmark. Runs until November 2.

Armonk Outdoor Art Show
Armonk
One of the premier juried outdoor art festivals in the region featuring hundreds of artists from across the country. Don’t forget to check out the 20 “Armonk has Heart” sculptures speckled across the town. Runs September 26-27.

Death by Chocolate Tea & Tour
Lyndhurst Mansion, Tarrytown, Multiple Time Slots Available
Victorian-inspired afternoon tea paired with a historic mansion tour and chocolate tastings.

Haunted Hudson Boat Tours
Riverfront Green Park, Peekskill, 7PM
Beginning October 2 and running every Friday and Saturday until the end of the month, New York Boat Co is making sure no spooky stone is left unturned. Local historian Jon Scott Bennett, will take travelers back through centuries of life along the river, from mysterious happenings and local legends to some of the darker stories that have become part of Hudson Valley lore.

New York Blood and Ink Tattoo and Horror Convention
Westchester County Center, White Plains, 3PM - 7PM
Back for another year, the convention, thrown by White Plains’ own Addicted to Ink tattoo shop, brings artists from across the country to Westchester. Notable tattoos this year are Nikki Simpson, Pon, and Courtney Raimondi, all of Ink Master fame. Event runs October 2-4, tickets required.

While the pumpkin spice latte still has its devoted following, local cafés are getting far more creative. This year's menus are filled with maple, brown butter, apple butter, toasted marshmallow, hazelnut, chai, and European-inspired flavors that feel right at home on a crisp morning. Whether you're looking for a classic PSL before apple picking or a more adventurous latte after a hike, these Westchester coffee shops are serving up some of the coziest drinks of the season. If you want to go the extra caffeinated mile, do a fall-crawl: start in Cross River and hit every cafe on your way down to the Sound Shore.

If your idea of fall leans more European café than pumpkin overload, Blue Heron should be your first stop. The Kirby Plaza cafe has become known for crafting thoughtful cups that go beyond the usual suspects. If you’re all coffeed’ out, Blue Heron has an impressive selection of loose leaf tea for a comforting cuppa–our favorite is the ginger-turmeric. Pair one with one of the café's rotating seasonal pastries or butternut squash quiche for the full experience.

Sometimes you just want something straight forward, and the creme brulee latte here doesn’t mince words–a rich caramel, steamed milk, espresso shots, and crunchy bits of sugar to top it all off. The cafe is the kind of place that feels made for lingering after a morning at Ward Pound Ridge or before heading to nearby orchards.

A longtime neighborhood favorite, Mandy Bean leans into comforting fall flavors without sacrificing its laid-back vibe. If you’re pumpkin-adverse, they have the perfect solution: the apple chai-der. Mandy Bean blends real apple cider and a chai blend for something seasonal, sans stereotypes.

The duo behind White Plains’ Ice Cream Social is now bringing caffeine to the community as well. Make your fall drink your way with the cafe’s latest housemade brown sugar cinnamon syrup. Will everything you drink taste like an apple cider doughnut? Absolutely…and there’s nothing wrong with that.

Pumpkin spice, crema edition? Sign us up. The cafe’s signature velvety, icy, coffee treat gets an autumnal twist. Enjoy on its own or top your favorite iced drink with it.

In addition to seasonal pumpkin pie brewed coffee, Tazza’s fall lineup also includes an iced pumpkin chai topped with sweet cream cold foam. If you're heading out for foliage, this is an easy and delicious detour.

For coffee purists, Ludy proves seasonal doesn't have to mean sugary. Known for its carefully sourced single-origin beans and beautifully prepared espresso drinks, the cafe’s minimalist space makes a great place to sit and sip. Go for the maple sea salt latte that’s a little sweet, a little savory, but extra comforting.

Community is as much a part of Casaroma's identity as coffee. The café regularly rotates seasonal beverages alongside specialty lattes—including customer favorites like its dulce de leche latte—so this month, order a pumpkin spice matcha, settle in with a good book, and enjoy the atmosphere.

Flour Power may be a bakery at its core, but it bolsters an impressive coffee menu and goes all out when it comes to specialty sips. This fall, indulge in everything from a pecan pie flat white, spiced apple cappuccino, or a caramelized banana latte. There quite literally is no wrong choice.

There's a reason apple picking has become synonymous with fall in New York. Fortunately, Westchester and the Hudson Valley (which is, for the record, actually upstate…) are home to some of the Northeast's best orchards. Some are perfect for families with corn mazes and petting zoos, others are ideal for couples looking for hard cider and mountain views, while a few remain refreshingly simple—just apples, fresh air, and a bag waiting to be filled.

Whether you're planning a quick afternoon close to home or making a full-day leaf-peeping road trip, here's where to pick your own apples this fall.

Stuart's Fruit Farm, Granite Springs
If you ask longtime Westchester residents where they've been apple picking since they were kids, chances are they'll mention Stuart's. Established in 1828, it's the county's oldest continuously operating farm and remains one of its most beloved fall traditions. Pick your own apples before browsing the bakery for pies, cider donuts, cookies, and fresh cider. The farm also offers pumpkins and plenty of photo-worthy fall scenery.

Wilkens Fruit & Fir Farm, Yorktown Heights
A county classic for more than 100 years, Wilkens grows dozens of apple varieties throughout the season, making repeat visits worthwhile. Families can also enjoy the corn maze, cider mill, bakery, and farm market before pumpkin season begins in earnest. Wilkens is especially popular in late September, when the widest selection of apples is available.

Harvest Moon Farm & Orchard, North Salem
Part orchard, part weekend festival, Harvest Moon has become one of the county's premier fall destinations. Along with pick-your-own apples, expect hayrides, live music, farm animals, seasonal food, local beer, and the farm's own Hardscrabble Cider. Keep an eye on the events calendar for what cool theme is popping up that weekend. It's an easy trip from New York City thanks to its proximity to the Metro-North station.

Outhouse Orchards, North Salem
Few orchards capture classic Hudson Valley views quite like Outhouse Orchards. Hit the fall festival for kids-friendly activities, the corn maze, farm stand, and spend the afternoon picking apples overlooking rolling hills. Outhouse is also home to one of the coolest fall photo-ops in the county: the pumpkin house.

Fishkill Farms, Hopewell Junction
For many locals, Fishkill Farms sets the standard for Hudson Valley apple picking. Its sprawling orchards feature dozens of heirloom and modern apple varieties, tractor rides, hard cider made from estate-grown apples, seasonal festivals, and some of the best mountain views in the region. During peak weekends, reservations may be required.

Barton Orchards, Poughquag
Think of Barton Orchards as the amusement park of apple picking. There are hundreds of apple trees—but there are also petting zoos, playgrounds, live music, food trucks, pig races, hard cider, and seasonal festivals nearly every weekend. Plan on spending the entire day here.

Greig Farm, Red Hook
If your ideal fall day involves fewer crowds and more scenery, Greig Farm is hard to beat. Family-owned since 1942, the farm offers pick-your-own apples, walking trails, Catskill views, hayrides, and everyone's favorite attraction: the pygmy goats waiting to be fed behind the farm market.

Rose Hill Farm, Red Hook
Historic charm meets modern cider culture at Rose Hill Farm. After picking apples, visitors can relax in the beautifully restored taproom serving estate ciders, wines, and rotating food trucks, all with sweeping Hudson Valley views.

Masker Orchards, Warwick
One of the most unique apple-picking experiences in New York, Masker allows visitors to drive directly into the orchard before parking beside the trees they're picking from. With roughly 20,000 trees spread across rolling hills, there's plenty of room to spread out–very main character moment, if we do say so ourselves.

Apple Dave's Orchards, Warwick
A Hudson Valley institution, Apple Dave's pairs U-pick apples with a relaxed atmosphere, bakery treats, and an on-site winery and distillery nearby, making it equally popular with families and couples.

Soons Orchards, New Hampton
Operating for more than a century, Soons is famous for its enormous apple selection, fresh pies, cider donuts, and farm market. The orchard has become a fall tradition for generations of Hudson Valley families.

Most orchards begin apple picking in late August, with peak season running from mid-September through mid-October. Early in the season you'll find varieties like Gala, Ginger Gold, and McIntosh, while Honeycrisp, Cortland, Empire, Fuji, and Granny Smith appear as the season progresses. Since availability changes weekly—and weather can affect harvests—it's always smart to check each orchard's website or social media before hitting the highway.

The sacred tradition of Riverfest has always been the true send off to summer. Local acts across three stages playing every genre from rock, to folk, to indie, bring the Westchester community together in a harmonious way (pun very intended). It’s an afternoon that doesn’t need a roadmap, you can simply listen, eat, and linger along the promenade.

Riverfest is also one of the region's largest outdoor shopping events, featuring more than 100 vendors selling handmade goods, artwork, jewelry, clothing, home décor, specialty foods, and gifts. It's an opportunity to discover Hudson Valley makers, local artists, and small businesses while supporting the community.

Don’t cut out early on Saturday–this year's closing lineup is designed to end the festival on a high note.

Beginning at 4:10 p.m., The Lady Gaga Experience featuring Haus of Monsters brings the energy of one of pop music's biggest stars to the waterfront. Complete with elaborate costumes, choreography and Gaga's chart-topping hits, the tribute show is expected to deliver the kind of spectacle that turns the festival's main stage into a concert experience.

At 5:20 p.m., legendary Bronx DJ Frankie Cutlass takes over for a full hour. A pioneer of New York's hip-hop scene, Cutlass has spent decades producing, remixing and performing alongside some of the genre's biggest names. His set is expected to keep the crowd dancing with a mix of hip-hop, freestyle and party classics that have made him a fixture of the city's music scene.

Closing out Riverfest from 6:30 to 7 p.m. is New York native and freestyle icon Lisa Lisa, whose string of '80s hits—including Head to Toe, Lost in Emotion and Can You Feel the Beat—helped define a generation of dance music. Her performance caps off a day of entertainment with the nostalgic sound that has remained a favorite among Yonkers audiences for decades.

A testament to his dedication to the city and hands-on approach, Mayor Mike Spano picked the headlining acts himself (and we have to say, he’s got great taste). Mayor Spano wanted artists capable of drawing a large, multigenerational audience while celebrating music with deep roots in the city's culture. Pairing a high-energy Lady Gaga tribute with a freestyle finale creates a balance of contemporary pop spectacle and hometown nostalgia—an approach that has consistently resonated with Riverfest crowds.

And if you’re really enjoying yourself, thank AJ–The 914 Collective’s blood, sweat, and more sweat coordinated artist outreach and worked directly with performers and their representatives to bring the entertainment to the Riverfest stage, helping turn the mayor's vision into one of the county's biggest attractions.

Admission to Riverfest is free, with no tickets or cover charge required. The annual celebration typically attracts 13,000 to 15,000 visitors so arrive early or take public transit if you can–parking fills up quickly.

For more info, check out yonkersdowntown.com/riverfest-2026-2

You were at the Mariano Rivera event at Walter’s last week, in line with a short girl and other man. I couldn’t get over your cheery disposition and striking good looks. I wanted to say hi but was so intimidated. Milkshake date soon? Meet you by the picnic tables…

Have a missed connection? Email us at [email protected]

Send them Not Upstate. Get three friends to sign up and we'll put two tickets to a Yonkers Brewing show in your name, your pick of the night.

See you in two weeks.

AJ & Cristiana
Not Upstate: A 914 Collective Magazine