[ Monthly Roundup / October 2026 ]
October Around Here: Things to Do in Warwick
The Warwick, New York area edition. Applefest weekend, haunted history, harvest live music, Witches Night Out, and the village Halloween parade.
[ About This Edition ]
This month's roundup covers the Warwick, New York area only: Warwick itself plus the surrounding Black Dirt communities like Pine Island, Florida, Goshen, and Greenwood Lake. The Milford, Pennsylvania area also gets its own edition this month, so if you are planning trips between the two regions, check the Milford roundup too. Every entry below was verified for 2026 against event organizers, the Village of Warwick, the Warwick Valley Chamber of Commerce, Sustainable Warwick, the Warwick Historical Society, Albert Wisner Public Library, and area farm and winery calendars.
October here opens with the village's biggest day of the year: Warwick Applefest on Sunday, October 4, when downtown fills with more than 150 craft and 75 food vendors and four music stages. Mid-month brings the Historical Society's Haunted History Tours over three nights and the pumpkin season at the region's orchards, and the month closes with Witches Night Out on Main Street and the village Halloween Costume Parade on the 31st. In between, there is weekend live music at the farms, cidery, and winery, a volunteer planting morning at Mountain Lake Park, and a library author talk to start the month.
[ The October Calendar ]
Events, organized by date
Virtual Author Talk: Veronica Roth
Thursday, October 1, 7:00 p.m.
Online via Albert Wisner Public Library, 1 McFarland Drive, Warwick, NY
Bestselling author Veronica Roth ("Divergent") joins a free virtual talk on courage, choice, and what comes next, hosted through the library's Speaker Consortium. Registration is free through the library's registration page, and it works as the month's book-minded opener before Applefest weekend.
RegisterHarvest Weekend Live Music at Pennings and the Winery
Saturday, October 3, and Sunday, October 4, afternoon sets
Pennings Cidery, 4 Warwick Turnpike, Warwick, NY, and Warwick Valley Winery and Distillery, 114 Little York Road, Warwick, NY
The first fall weekend of live music around the Valley: the Missy Ping Band plays the Pennings Cidery Saturday, 3 to 6 p.m., and OC5 follows Sunday, 3 to 6 p.m., both with a $5 cover, while the Warwick Valley Winery runs its regular weekend sets from 1 to 5 p.m., with Vera and the Force on Sunday. Note that the winery charges per-car admission on September and October weekends; the Pennings music schedule and the winery's live music page have the full details.
Pennings Cidery music • Winery music calendarWarwick Applefest
Sunday, October 4, 9:00 a.m. to 5:00 p.m.
Downtown Warwick, along Main Street, Railroad Avenue, and the village parks
The signature event of the month and Orange County's largest one-day autumn festival, presented by the Warwick Valley Chamber of Commerce since 1989. More than 150 craft vendors, 75 food vendors, four live music stages, apple pie baking and eating contests, a children's carnival, a farmers market, and 50-plus local nonprofit exhibitors fill the downtown streets. Admission is free, and proceeds benefit the Chamber and dozens of local nonprofits. Plan to walk or park on the outskirts; the village closes its core to traffic. Albert Wisner Public Library is closed that day, so library trips should wait for another day.
Learn morePauly Di Dio at Pennings Farm Market
Friday, October 9, 6:00 to 9:00 p.m.
Pennings Farm Market, 161 State Route 94 South, Warwick, NY
Friday-night live music at the farm market, part of Pennings' weekly fall music run into November. It is an easy evening stop after a day of apple picking, and the farm's site posts the weekly lineup.
Learn moreThe Possums at Pennings Cidery
Saturday, October 10, 3:00 to 6:00 p.m.
Pennings Cidery, 4 Warwick Turnpike, Warwick, NY
Weekend live music continues at the cidery with The Possums, 3 to 6 p.m., $5 cover. Columbus Day weekend trips to the Warwick orchards and trails can wrap up here.
Learn morePollinator Pathway Volunteer Planting Day
Tuesday, October 13, 9:00 to 10:00 a.m.
Mountain Lake Park, 46 Bowen Road, Warwick, NY (meet near the pickleball courts)
Sustainable Warwick's Pollinator Pathway committee leads a weekday volunteer hour at Mountain Lake Park: clearing invasive plants and planting native pollinator species around the park's edges. It is a short, hands-on volunteer morning, and organizers ask for an RSVP in advance through the Sustainable Warwick site.
Learn moreHaunted History Tours with the Warwick Historical Society
Friday, October 16, 5:30 to 8:30 p.m., with additional nights Saturday, October 17, and Sunday, October 18
Begins at the A.W. Buckbee Events Center, 101-105 Main Street, Warwick, NY
The Historical Society's immersive walking tours of Warwick's history and lore run over three October nights, starting at the Buckbee Events Center with autumnal snacks and a small market. Past editions have run about $40 to $50 depending on tier, with a $100 VIP option that adds after-hours time at Baird's Tavern; the tours are rated PG-13, and general tickets went on sale September 21. They sell out most years, so reserve through the society's calendar.
Learn morePumpkin Palooza at All One One All Farm
Saturday, October 17, from noon
All One One All Farm, 221 Craigville Road, Goshen, NY (about 25 minutes west of Warwick)
The regenerative farm and education center in Goshen holds its pumpkin-season community cooking competition: home cooks enter their best sweet and savory pumpkin and winter squash dishes, and visitors join in as tasters, voting for the People's Choice alongside guest judges. Tickets run a few dollars; the official farm event page has the details, and it is a low-key way to spend a fall afternoon in the county's farm country.
Learn moreThe CruZadors at Pennings Farm and Orchard
Saturday, October 24 (band time posted on the Pennings events page)
Pennings Farm and Orchard, Warwick, NY
The farm's weekend music slate continues late in the month with The CruZadors at the orchard, one of the last outdoor-music Saturdays before the season winds down. Check the Pennings site for the set time.
Learn moreThe Bunker Boys at Warwick Valley Winery and Distillery
Sunday, October 25, 1:00 p.m.
Warwick Valley Winery and Distillery, 114 Little York Road, Warwick, NY
Late-October live music at the winery with The Bunker Boys, part of the winery's regular fall weekend lineup. Winery weekends in September and October carry a per-car admission, and pick-your-own apples run through mid-November, so it is a full orchard-visit day.
Learn moreWitches Night Out on Main Street
Thursday, October 29, 3:00 to 8:00 p.m.
Main Street, Village of Warwick, NY
The merchants' Halloween evening downtown, organized by the Warwick Merchants Collective under the Chamber: participating shops and restaurants along Main Street host specials and raffles for an evening of dining, sales, and spooky fun. It is a useful warm-up for the costume parade two nights later, and the Chamber's merchant page lists the participating businesses.
Learn moreWarwick Halloween Costume Parade
Saturday, October 31; lineup 4:30 p.m. on High Street, step-off 5:00 p.m.
From High Street down Main Street to Railroad Avenue, Warwick, NY
The Village of Warwick Recreation Department and the Warwick Lions Club present the annual Halloween Costume Parade on Halloween evening: marchers step off at 5:00 p.m. and walk down Main Street to Railroad Avenue, followed by a costume contest with prizes for Most Original, Scariest, Best Group or Family, and Cutest. The village posts that evening's curfew and road closures in its "All Things Halloween" notice, so check it before planning the night.
Learn more[ Around Here Picks ]
Five to plan around this month
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OCT 4 • DOWNTOWN
Warwick Applefest
The village's biggest day: 150-plus craft vendors, 75 food vendors, four music stages, pie contests, and a children's carnival, all free to enter. See the full entry above.
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OCT 16-18 • MAIN STREET
Haunted History Tours
Three nights of immersive walking tours with the Historical Society, starting at the Buckbee Events Center. They sell out most years, so tickets are the thing to book early this month.
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OCT 31 • 4:30 P.M.
Warwick Halloween Costume Parade
The village's Halloween tradition: costumes gather on High Street at 4:30, step off at 5:00, and finish with a prize contest at Railroad Avenue. Check the village's curfew notice before heading out.
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OCT 29 • MAIN STREET
Witches Night Out
An evening of shop specials, raffles, and spirit on Main Street from the Warwick Merchants Collective, two nights before the parade.
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OCT 1 • 7 P.M.
Virtual Author Talk with Veronica Roth
Bestselling author of "Divergent" in a free evening talk through the library. Register ahead through the library's consortium page; it is the month's easiest literary stop.
[ Recurring Events ]
Every week this month
Warwick Valley Farmers' Market
Sundays, 9:00 a.m. to 2:00 p.m., May through November (October dates: 4, 11, 18, 25)
Local farms and producers from the Black Dirt region set up weekly in the South Street parking lot downtown, rain or shine. Note that the October 4 date falls on Warwick Applefest Sunday, when the downtown core fills with festival vendors, so confirm that week's market setup on the listing before you plan a trip.
Market detailsLive Music at the Warwick Valley Winery
Weekends, 1:00 to 5:00 p.m., with per-car admission in September and October
The winery runs live music every weekend through the fall; October acts already posted include Vera and the Force on October 4 and The Bunker Boys on October 25. Pick-your-own apples run seven days a week, 11:00 a.m. to 5:00 p.m., through mid-November at about $40 per half-bushel bag.
Winery calendarAlbert Wisner Public Library programs
Throughout October, at 1 McFarland Drive, Warwick (the library is closed Sunday, October 4, for Applefest)
Recurring weekly programs include Mahjong on Tuesdays, the Tuesday Evening Book Group, Duplicate Bridge on Wednesdays, Dungeons and Dragons for Adults on Thursdays, story times, and more. The library publishes the full month on its own Programs calendar.
Library calendarPennings Farm Market and Cidery
Seven days a week through apple season, at 161 State Route 94 South and 4 Warwick Turnpike, Warwick
U-pick apples run through October, with hayrides, pony rides, face painting, and pumpkin picking, plus the farm's live music slate on top. Individual music dates are on the Pennings events page.
Pennings detailsApple Dave's Orchard and Distillery
Through the end of October, at 82 Four Corners Road, Warwick
Apple picking runs through the end of October with weekend live music, pick-your-own pumpkins, wagon rides, puppet shows, and the farm's country store and distillery. The region's April freeze damaged parts of the crop, so the orchard is supplementing tree-picked apples with bagged New York apples and picking bins; check the farm's site for what is available when you visit.
Apple Dave's details[ Family & Community ]
Gatherings, kid-friendly programs, and community events
- Warwick Applefest (Oct 4): the free downtown festival with a children's carnival, pie baking and eating contests, and four music stages.
- Halloween Costume Parade (Oct 31): the village parade and costume contest on Halloween evening, with categories for Most Original, Scariest, Best Group or Family, and Cutest.
- Pumpkin Palooza (Oct 17): the community pumpkin cooking competition at All One One All Farm in Goshen, where visitors taste entries and vote.
- Pollinator Pathway planting morning (Oct 13): the nine-to-ten a.m. volunteer hour at Mountain Lake Park with Sustainable Warwick; RSVP requested.
- Pennings fall days: u-pick apples with hayrides, pony rides, and face painting through October, plus weekend and Friday-night music at the farm market and cidery.
- Library programs: story times, book groups, Mahjong, bridge, and Dungeons and Dragons run weekly at Albert Wisner Public Library all month.
[ Outdoor & Seasonal ]
Apple season and autumn color
October is the heart of apple season in the Black Dirt region. Our outdoor and seasonal guide gathers the trails and parks of the region: Sterling Forest State Park, Wawayanda State Park, and the village's parkland, all open daily through the fall. Meanwhile the orchards around town are picking through the month: the Warwick Valley Winery's pick-your-own runs through mid-November, Pennings offers u-pick apples with hayrides and pony rides, and Apple Dave's runs picking plus pumpkins, wagon rides, and weekend live music through the end of October. Note that this year's April freeze affected the regional crop, so check each farm's site for availability before you go.
For a dated outdoor program, the Pollinator Pathway planting morning on Tuesday, October 13 (9 to 10 a.m. at Mountain Lake Park) is a short volunteer hour that gets you outside with purpose; see the full entry above for the link.
Sterling Forest State Park and Wawayanda State Park are the large public lands closest to Warwick, with miles of trails, lakes, and overlooks open every day through the fall, and foliage typically peaks around the middle of the month.
New to the area? Our New to the Area guide covers what life is like around Warwick and the Black Dirt region, and the Warwick community guide goes deeper into the history, dining, shopping, and annual events. The Warwick area events page carries the year-round event calendar, and the monthly roundup archive holds every past edition.
Event details can change, including dates, times, locations and admission requirements. Please confirm details with the event organizer before heading out.