Pawsitive Spots

Beacon Bonfire Music + Art Festival
2025-11-05 19:00 - 2025-11-09 18:00 (America/New_York) | NY
Beacon Bonfire Music + Art Festival was born from the glow of a campfire. In the midst of the Covid era, 100 members of our creative community gathered to share warmth, music, and hope. That spark became the foundation of a festival that now transforms Beacon, NY, into a vibrant stage for connection and creativity.
By 2023, the fire had grown—welcoming more than 4,000 festival-goers from across the Hudson Valley, NYC, and beyond. Together, we celebrated the talents of over 400 artists—musicians, dancers, makers, and dreamers—whose work reflected the heartbeat of our community.
Today, Beacon Bonfire has become a cultural cornerstone—an annual gathering where earthy and cosmic energies intertwine, where art and music burn brightly, and where community thrives. In 2025, we’re honored to be recognized as one of the top three festivals in Chronogram’s Readers’ Choice Awards for Best Music Festival.
The fire that began with a single circle continues to expand—drawing us closer, inspiring us to move, create, and imagine together.

Beacon Bonfire is family-friendly (including pets); however, not all venues allow pets. It can be crowded, so many dogs might not feel good attending this event.

Belleayre Annual Fall Festival
2025-10-11 10:00 - 2025-10-12 17:00 | Belleayre Mountain, 181 Galli Curci Road, Highmount, NY, 12441, United States
The oncoming winter will be arriving soon, and we’re celebrating with our official send-off to the summer season at our annual Fall Festival. Both weekends will be jam packed with fun-filled activities for the entire family! Feast your taste buds, eyes, and other senses with dozens of local food, beverage, and craft vendors highlighting the unique culture native to the Catskills & Hudson Valley. Live music will float through the cool air all day, and the sights will be truly one-of-a-kind with a fall foliage-filled Scenic Gondola Ride. The kids will be thoroughly entertained with fun lawn games, arts & craft activities such as decorate a pumpkin, and more! As always, it will be a fantastic two weekends, and we look forward to seeing you on the mountain for our official pre-winter get together. We encourage our furry friends to visit our fall fest! We do ask that they keep their owners leashed while here.
Kid’s Entertainment | Live Music | Craft Vendors | Food | Scenic Gondola Lift Rides | & More!

Windham's 31st Annual Autumn Affair
2025-10-11 10:00 - 2025-10-12 17:00 | NY
Celebrate the vibrant colors of fall in the Gem of the Catskills at the 31st Annual Autumn Affair, happening Columbus Day weekend, October 11 & 12, 2025, from 10 AM to 5 PM daily. This beloved Catskills tradition brings friends, neighbors, and visitors together for two days of live music, delicious food, unique shopping, and family fun.
Main Street will come alive with more than 50 vendors offering local crafts, seasonal treats, and specialty foods, plus sidewalk sales from Windham’s Main Street businesses. Festival highlights include hay wagon rides, axe throwing, chainsaw carving demonstrations, and kid-friendly entertainment. Don’t miss the Coldwell Banker’s Doggie Beauty Contest, which will be held both days during the event.
Free parking is available at Windham Mountain Club and throughout town, and admission is free so bring the family, explore the festivities, and enjoy the beauty of autumn in the Great Northern Catskills.

Spirit of Beacon Day
2025-09-28 11:00 - 17:00 | Beacon’s Main Street, Main Street, Beacon, NY, United States
The Spirit of Beacon Day is a beloved annual community celebration held on the last Sunday of September. Since 1977, this volunteer-run event has brought the city together with a mission to foster unity and connection among residents. The day is a vibrant showcase of Beacon’s spirit, featuring a lively parade down Main Street with participation from local schools, community groups, and non-profits.

Beyond the parade, the day is filled with vendor tables offering a variety of food, crafts, and information about local services and organizations. Attendees can enjoy live music and performances on multiple stages, as well as a wide range of family-friendly activities. It’s a perfect opportunity to celebrate Beacon’s unique character and get to know the people who make it a special place to live.

Weekend Food Trucks at Millbrook Vineyards & Winery
2025-09-27 12:00 - 2025-09-28 18:00, 2025-09-13 12:00 - 2025-09-14 19:30, 2025-09-06 12:00 - 2025-09-07 18:00 | Millbrook Vineyards & Winery, 26 Wing Road, Millbrook, NY, 12545, United States
Savor the perfect pairing of wine and food at Millbrook Vineyards & Winery’s Weekend Food Trucks event. Throughout the season, a rotating lineup of the Hudson Valley’s best food trucks sets up shop at the winery, offering a diverse array of delicious fare. Enjoy stunning vineyard views as you find a spot on the lawn or Taproom Terrace. The event features live music and, of course, a full selection of Millbrook’s award-winning wines, available by the glass or bottle. With a relaxed, dog-friendly atmosphere, it’s an ideal way to spend a beautiful day enjoying great food, live entertainment, and exceptional wine.

Sleepy Hollow Street Fair
2025-09-21 10:00 - 16:00 | NY
he Sleepy Hollow Street Fair, presented by the Sleepy Hollow Tarrytown Chamber of Commerce, is a vibrant community event that takes over Beekman Avenue. This annual street fair features over 145 arts and crafts, food, and beverage vendors, as well as local shops and eateries.

The fair is a festive, family-friendly event with live music, a kids’ zone, and entertainment for all ages, including a special appearance by the Headless Horseman. It’s a popular attraction that draws thousands of people and is a great way to kick off the autumn season in the historic town.

ENTERTAINMENT LOCATION & SCHEDULE
* Headless Horseman: in front of Ganso Ramen on Beekman Avenue & Route 9/Broadway
* Witches Along The Hudson: Beekman Avenue & Pocantico Street
* Greg Jacquin Band Duos: in front of 38 Beekman Avenue Lot
* Luis Enrique’s Andean Flutes Band: Beekman Lot at the top of Beekman and Rte 9
* Little Sparrow Face Painting: Beekman Lot Kids Zone
* Village of Sleepy Hollow Kids’ Zone: located at Beekman Parking Lot

Weekend Food Trucks and Free Live Music
2025-09-20 12:00 - 2025-09-21 19:00 | Millbrook Vineyards & Winery, 26 Wing Road, Millbrook, NY, 12545, United States

Summer Sundays on Cannon Block
2025-09-14 14:00 - 18:00 | King’s Court Brewing, 40 Cannon Street, Poughkeepsie, NY, 12301, United States
Save the dates for these fun, all-ages Summer Sundays on Cannon Block Parties, now in their fourth summer! Enjoy food trucks, live music, games, craft beer, wine and cider, and more.
Downtown Poughkeepsie — come for the vibe, stay for the scene!
2025 music lineup
• June 8: Myles Mancuso Band
• July 13: Good Time Honey Band
• Aug. 10: Kale Band
• Sept. 14: The Classics – Funk Band
(These are weather-dependent events, and there are no rain dates)

Farm Fest with NOFA-NY
2025-09-14 11:00 - 17:00 | Fishkill Farms, 9 Fishkill Farm Rd, Hopewell Junction, NY, 12533, United States
NOFA-NY (Northeast Organic Farming Association of New York) and Fishkill Farms are teaming up to host Farm Fest ’25!
Farm Fest is dedicated to celebrating local communities while advocating for a sustainable regional food system that’s ecologically sound, socially just, and economically viable. Join us for a fun day on the farm to learn from a variety of organic farmers and advocates by educational talks and demonstrations, as well as visiting the vendors, farm store, cider bar, and more!
Reservations are needed to participate in pick-your-own.

San Gennaro Festival
2025-09-13 14:00 - 17:00 | Robibero Winery, 714 Albany Post Road, New Paltz, NY, 12561, United States
Mark your calendars for Saturday, September 13, 2025, for a day of delicious food, great music, and dog-friendly fun at Robibero Winery.

Celebrating the traditional San Gennaro Festival with a special focus on pizza and fresh mozzarella making, Robibero Winery will have special mozzarella demonstrations by Vinny’s Deli in Pawling, and Boar’s Head, represented by Dutchess Provisions, will be on-site giving out samples. What’s Poppin’ Kettle Korn will also be there, along with many other vendors! The wood-fired oven will be going all day, serving up delicious pizzas.

In addition to the food, :

Live Music from 2pm-5pm
Wine Tasting, Wine by the glass/bottle, Craft NYS Beer & Craft Cocktails
Nonalcoholic wine by the glass/bottle
Lawn Games
Bonfire
Family Friendly/Pet Friendly atmosphere

The event is free, and no reservations are required. It’s happening rain or shine! They have plenty of covered seating on our large deck, under our tent, and inside the tasting room. Tables are first-come, first-served.

Riverfest
2025-09-13 12:00 - 19:00 | Yonkers Downtown, 66 Main Street, Yonkers, NY, 10701, United States
Riverfest, presented by the Yonkers Downtown BID, is the largest one-day festival in Westchester County. Held annually in September, this free event transforms the downtown Yonkers waterfront into a vibrant hub of activity for over 15,000 attendees.

The festival features multiple stages with live music spanning various genres, including jazz, soul, hip-hop, rock, and more. Visitors can enjoy a diverse culinary experience with over 100 food vendors offering cuisine from around the world, as well as unique arts and crafts vendors.

Riverfest is a family-friendly event with a dedicated Kid Zone, rides, games, and other activities. It’s a celebration of the city’s energy, diversity, and community, and is held rain or shine.

Family Fun Weekend
2025-09-06 11:00 - 2025-09-07 18:00 | Barton Orchards, 63 Apple Tree Ln, Poughquag, NY, 12570, United States
Bring the family for a weekend of fun at Barton Orchards! This family-friendly event features a wide range of activities for all ages. Enjoy classic farm fun like hayrides, and getting lost in the corn maze. The Fun Park offers exciting attractions, including a giant slide, pedal go-karts, mini golf, and apple cannons. You can also visit the petting zoo, a playground, and catch a live show. Of course, no visit to Barton Orchards would be complete without picking your own fresh apples and other seasonal produce. While you’re there, be sure to grab a treat from the farm market and enjoy live music.

Modern Makers Market
2025-09-06 11:00 - 2025-09-07 17:00 | NY
The Modern Makers Market by Hops on the Hudson is a free, outdoor event held in Cold Spring, NY, on the lawn of St. Mary’s Episcopal Church. Occurring from May to November, the market features over 60 artisans and artists selling a wide variety of handcrafted and small-batch goods, including woodworking, jewelry, pottery, textiles, and more. The market also includes three food trucks, live music, and is dog-friendly and accessible via Metro-North train. A key component of the market is its “All Donations Help” program, which financially supports four local non-profit organizations that assist those in need in the Hudson Valley.

Adress:
Lawn of St. Mary’s Episcopal Church
1 Chestnut St POB 351,
Cold Spring, NY 10516

Fall Harvest Festival
2025-09-06 10:00 - 2025-09-07 17:00 | Fishkill Farms, 9 Fishkill Farm Rd, Hopewell Junction, NY, 12533, United States
Join Fishkill Farms for their annual Fall Harvest Festival! Every weekend in September and October, the farm is packed with autumnal fun. You can pick your own sustainably grown apples and pumpkins, take a scenic wagon ride through the orchard, or get lost in their corn maze. The festival also features live music from local bands, delicious food from the outdoor grill (including Jamaican Jerk Chicken and apple cider donuts), and hard cider from the Treasury Cider Bar. You can also visit the farm store for homemade pies, fresh produce, and other local goods. Please note that while visiting the farm store, cider bar, and live music is free, you will need a reservation and ticket for pick-your-own, wagon rides and access the corn maze.

Friday Night Food Trucks
2025-09-05 17:00 - 20:00 | Millbrook Vineyards & Winery, 26 Wing Road, Millbrook, NY, 12545, United States
Celebrate the start of the weekend at Millbrook Vineyards & Winery’s Friday Night Food Trucks event! Take advantage of the stunning sunset views from their Taproom Terrace as you enjoy a rotating selection of delicious, family-friendly fare from local food trucks. With live music from local performers, a wide selection of Millbrook’s signature wines available on tap, and other beverages including beer and non-alcoholic options, it’s the perfect casual outing. Bring a blanket or chairs to relax on the sprawling lawn and soak in the beautiful vineyard atmosphere.
