🎃 Sleepy Hollow's Twilight Village Opens... Beware the Headless Horseman!

🎃 Twilight Village at Sleepy Hollow
Fri.-Sun., Oct. 2-31 | Philipsburg Manor, Sleepy Hollow | Evenings from 6 or 6:30p | $25-$35
 
Historic Hudson Valley turns Philipsburg Manor into an after-dark village where the Legend lives. Mingle with Ichabod Crane and Katrina Van Tassel, meet storytellers, fire performers, and fortune tellers, and sip cocktails from the food trucks, all before the Headless Horseman makes his ride. All ages, advance tickets only.
Wander the Legend after dark, if you dare meet the Horseman →
 
🎸 Sleepy Hollow Music Festival
Sat., Oct. 3 | Kingsland Point Park, Sleepy Hollow | 12p-8p | $62.50+
 
A day-long, Halloween-themed music festival in the legendary village, with two stages and no overlapping sets. The Main Stage features Everclear, the Smithereens with Marshall Crenshaw, Fastball, and more. Add a costume parade, a Headless Horseman, a huge Kids' Zone, food trucks, a Makers' Market, and beer gardens. Kids 12 and under free with an adult.
Everclear, a Headless Horseman, and the best Halloween party in the Hudson Valley →
 
🦪 Oyster Fest at The Sailhouse
Sundays in Oct. | The Sailhouse, Tarrytown | 12p-6p
 
The waterfront Tiki Bar and patio fills with fresh oysters, seasonal food, cocktails, and live music over the Hudson. This Sunday, Oct. 4, brings the Candy Shop Band, an oyster slurp-off for a Sailhouse gift card, beer, wine, and spirits tastings, and a visit from the Headless Horseman himself.
Slurp oysters on the Hudson and dodge the Horseman, every Sunday →

 
Have an event you want to feature in Loving Westchester?

🍺 Friday Night Live: Oktoberfest, Parade and Fireworks
Fri., Oct. 2 | Main Street and Boulanger Plaza, Hastings-on-Hudson | 6p-8p | Free
 
Live polka from Polkadelphia, plus food and drinks from local Hastings businesses. At 8p, an America 250 Salute to Service Parade honors veterans, first responders, and Village staff, followed by a fireworks display at MacEachron Waterfront Park at 8:45p.
 
🎃 Pelham Children's Center Pumpkin Festival
Sat., Oct. 3 | Pelham Town House, Pelham | 9a-2p | Adults free, ticket prices vary
 
A fall fundraiser with a pumpkin patch, carnival rides and games, a used-book sale, and food trucks. Free coffee from Shea Station and water. Onsite ticket sales close at 1p.
 
🏷️ Hastings Village-Wide Fall Tag Sale
Sat., Oct. 3 | Throughout Hastings-on-Hudson | 10a-4p | Free
 
Participating homes across the Village sell furniture, clothing, household goods, toys, bikes, books, collectibles, and sports equipment. A day of neighborhood treasure hunting.
 
🎃 Peekskill Rotary Fall Festival
Sat., Oct. 3 | Riverfront Green Park, Peekskill | 11a-5p | Free
 
A community festival on the waterfront with a DJ and dancing, food trucks, local art and craft vendors, raffles, a pumpkin patch, and children's activities including pumpkin painting, a kids' maze, and inflatables. Free parking, dog friendly, rain or shine.
 
🎃 Town of Mamaroneck Fall Festival
Sat., Oct. 3 | Memorial Park, Larchmont | 12p-4p | Free
 
A fall day at Memorial Park with a pumpkin patch, a new Larchmont Nurseries maze, Touch-A-Truck, face painting, a bounce house, live music from School of Rock and Sway, adoptable dogs, and food trucks.
 
🍺 Croton Oktoberfest
Sat., Oct. 3 | Grand Street, Croton-on-Hudson | 12p-6p | Free
 
The Croton Business Council's Oktoberfest in the Upper Village, with over 65 artisanal food, drink, and retail vendors, plus a kinder-fest area with bouncy houses for kids. Free shuttle from Croton-Harmon station all day.
 
🎸 Steinyfest
Sat., Oct. 3 | Larchmont Train Station | 3p-10p | $50+
 
A seven-hour outdoor music festival in the upper Metro-North lot, headlined by The Stews with Illiterate Light, Copilot, Pete Francis, Tyler Miller, and Christine Chanel. All ages, free parking.
 
⚽ Westchester Soccer Club vs. AV Alta FC
Sat., Oct. 3 | The Stadium at Memorial Field, Mount Vernon | 7p | $10+
 
Westchester SC returns home to host California’s AV Alta FC in USL League One action. Doors at 5:30p, free parking, all ages.
 
🇯🇵 Japan Fes
Sun., Oct. 4 | Ridge Road Park, 287 Ridge Rd., Hartsdale | 10a-6p | Free admission
 
A Japanese festival at Ridge Road Park with 15+ vendors serving ramen, katsu sandwiches, gyoza, mochi and so many more cultural delicacies.
 
🌶️ Rye Annual Chili Cook-Off
Sun., Oct. 4 | Rye Rec, 281 Midland Ave., Rye | 12p-4p | $25
 
Rye Chamber's chili cook-off features tastings from local home cooks and restaurants, a People's Choice vote, live music from Rye High School bands, pumpkin decorating, cornhole, food trucks, and local beer. Benefits the Chamber's scholarship fund.
 
🎸 Fall Festival at Harvest Moon
Sat.-Sun., Oct. 3-4 | Harvest Moon Farm and Orchard, North Salem | 9a-5p | $25 online, $30 gate
 
Apple picking, a pumpkin patch, hay rides, cider donuts, hard cider, BBQ, and a Fun Zone with an obstacle course and Farm Hoppers, with live country music across the weekend. Kids 3 and under free.
 
🏮 Autumn Glow Festival
Evenings, dates via ticket selector | Glen Island Park, New Rochelle | 6:30p-10p | $18.99+
 
A nighttime walk through hundreds of hand-crafted Chinese lanterns lit by LED, each telling a story, with local food, drink, and photo ops throughout. All ages, children 3 and under free. Arrive after sunset for the best light-trail experience.

🖋️ Westchester New York Tattoo Convention
Fri.-Sun., Oct. 2-4 | Westchester County Center, White Plains | Fri. 3p-10p, Sat. 11a-10p, Sun. 11a-7p | Ticket prices vary
 
The 10th annual Blood and Ink convention brings hundreds of tattoo artists from around the world, piercing, vendors, sideshow acts, musical performances, and more. Kids 12 and under, veterans, police, fire, and EMS get in free.
 
🎷 Jazz Night at The Witch
Fri., Oct. 2 | The Good Witch Coffee Bar, Hastings-on-Hudson | 8p-10p | Free admission
 
The Good Witch reopens for the evening with quartet-style jazz from New Rivertown Sound, drinks, and bites, plus a patio view of the Hastings fireworks at 8:45p.
 
🍺 Soul Brewing Oktoberfest
Sat., Oct. 3 | Soul Brewing Company, 41 Wheeler Ave., Pleasantville | 1p-10p | Free admission
 
An Oktoberfest celebration at the award-winning Soul Brewing in Pleasantville with beer, food from FarmEats, commemorative steins, and live polka music.
 
🔍 The Great New Castle Hunt
Sat., Oct. 3 | Greeley House, Chappaqua | 1:30p-6p | $50+
 
A competitive scavenger hunt where teams solve clues and trivia around Chappaqua by car and on foot using a mobile app, followed by a catered BBQ with beer and wine at the historic Greeley House. Ages 21+, benefiting the New Castle Historical Society.
 
😂 Women Together Comedy Fundraiser
Sat., Oct. 3 | The Good Witch Coffee Bar, Hastings-on-Hudson | 7p-9p | $30
 
A stand-up fundraiser bringing together women comedians in support of Women Together Global, a non-profit focused on economic and educational empowerment of women and girls around the world.
 
🎭 Randy Feltface: Gimmick
Sat., Oct. 3 | Tarrytown Music Hall, Tarrytown | 8p | $42+
 
The purple-felt puppet comedian, seen on Netflix and NBC's Bring The Funny and nominated for Best Comedy at the Edinburgh Fringe, brings his stand-up show Gimmick to Tarrytown.

Got 99 ideas, but can’t execute 1?

 
Hit me.

 
Hey, everybody. This is Bec.
 
I’ve spent 20 years helping businesses, brands and community organizations grow through better strategy, communications and partnerships. If you’re a local business owner with 100 ideas but never enough time to move them forward, that’s exactly why I created QueenBHive. Think of me as the person in your corner. Helping you decide what matters most, connecting the right dots, creating momentum, and making sure the good ideas actually happen. Whether that’s your visibility, social content, a launch, a partnership or simply having someone strategic to think alongside.
 
Send me a message and let me be your WingWoman.

🎶 Stayin' Alive: A Tribute to the Bee Gees
Fri., Oct. 2 | Palace Theatre, Stamford, CT | 8p | $25+
 
A full Bee Gees tribute running through "Stayin' Alive," "Night Fever," "How Deep Is Your Love," and the ballads, with big-screen video clips and imagery.
 
😂 Maddy Smith
Sat., Oct. 3 | Levity Live, West Nyack | 6:30p and 9p | $27.53+
 
The fast-talking NYC comedian and seven-season Wild 'N Out regular brings her Bad Genes Tour and a new hour of material for two shows, with roasts aimed at the front row.
 
🍶 Third Anniversary Celebration at Dassai Blue
Sat.-Sun., Oct. 3-4 | Dassai Blue Sake Brewery, Hyde Park | 11a-5p | Free
 
The Hyde Park sake brewery marks three years with a weekend of special sake tastings, a one-weekend-only Type 35 Nama, a tuna cutting with fresh otoro sushi after, a craft market, Japanese food pop-ups, and brewer presentations. No reservation needed.