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Top 10 Events in October

Date Published: September 16, 2021

Notes of fall are in the air and we're super excited for all the seasonal festivities ahead! From spooky soirees to artful weekends, check out what's happening in October in Dutchess.


1. Oktoberfest Handcrafted Fair

Saturday, October, 2 10:00 a.m. to 6:00 p.m & Sunday, October 3 from 10:00 a.m. to 5:00 p.m. at Dutchess County Fairgrounds, Rhinebeck

Quail Hollow Events is bringing an artfully reimagined Octoberfest to the Hudson Valley! Their second annual Handcrafted Octoberfest: A Family Harvest Celebration returns to Rhinebeck’s Dutchess County Fairgrounds. This open-air event honors harvest time and slips in a few Germanic traditions, but is centered around the concept of handmade goods and arts. From Hudson Valley’s best craft beer, wine and spirits to seasonal grub, live musical performances, and expert-led harvest activities, there’s something for every generation and tastebuds. The festival will also offer a carefully curated collection of handmade goods in different media, complemented by a diverse selection of autumnal extras like fine art pumpkin carving. Catch special events like the Wild World of Animals Show by Two by Two Animal Haven on Saturday, and Fritz’s Polka Band and yodeling competition on Sunday. For the full entertainment and more details click here.


2. Barn Star Antique Show

Saturday, October 9 from 10:00 a.m. to 5:00 p.m. - Sunday, 11:00 a.m. - 4:00 p.m. at Dutchess County Fairgrounds, Rhinebeck 

The Dutchess County Fairgrounds will once again host this iconic event in the three, spacious and well-ventilated buildings. What you will find at the show spans not only centuries but cultures as well.  Shop from Oriental rugs to fine, designer and costume jewelry, American and Continental furniture, fine porcelain and ceramics amongst much more. With over 125 vendors spanning centuries, there’s a unique find for everyone. Food trucks will also be on site. For more information, click here.  


3. Boos and Brews

Friday, October 15 from 5:00 p.m. to 10:00 p.m at Barton Orchard, Poughquag 

Join Barton Orchards for their adult-friendly event of the season, Boos and Booze Drag Show, hosted by Summer Orlando and Barbara Streetsand!  Tickets include a live singing drag show and access to their Jack O' Lantern trail. Come in your spookiest costume to enter their contest with a cash prize for the winner. Grab some friends, a BOOZY drink and join the fun on the farm! For more information, click here

4. New York State Sheep and Wool Festival

Saturday, October 16 from 9:00 a.m to 5:00 p.m. and Sunday, October 17 from 9:00 a.m to 4:00 p.m. at Dutchess County Fairgrounds, Rhinebeck 

The Northeast’s thriving sheep industry is showcased and celebrated each year in this famous festival that draws a multitude of visitors from across the country to the lovely village of Rhinebeck. Prepare for a slightly scaled-back, hybrid event this October. Vendors will be placed throughout buildings and outside, leaving room for proper spacing and distancing. Your day will include fiber artists and crafts galore, amazing sheep herding demonstrations, frisbee dogs, and a petting zoo. No in-person workshops will be taking place, but a curated selection will be available to take virtually on the Thursday and Friday of that week. You’ll also find demonstrations, farm tours, and other educational videos online, as well as a handful of vendors offering virtual sales via their website.


5. ArtEast Open Studio Tours

Saturdays - Sundays, October 16-17 & 23-24 at various locations in Dutchess County 

Take a fall road trip through Dutchess County for the annual  ArtEast Open Studio Tours. Hit towns like Dover Plains, Amenia, Poughquag, Lagrangeville, Hopewell Junction, and Pawling to meet with artists and explore their creative space. Virtual exhibits are also available online. To see a full list of participating artists, studios, and galleries as well as special kick-off events, click here


6. Beacon Sloop Club Annual Pumpkin Festival 

Sunday, October 17 from 12:00 p.m. to 5:00 p.m. at Pete & Toshi Riverfront Park

The Beacon Sloop Club Annual Pumpkin Festival is back and is highlighting Hudson valley pumpkins of all sizes & shapes! Freshly baked pumpkin pie, pumpkin soup, cider, and other delights will be available. Two solar power stages with live music and many free children's activities, environmental displays will be happening throughout the day. Explore the Hudson River and take free sails on the Woody Guthrie. Visitors should arrive at noon to sign up for sails weather permitting. For more information, click here.


7. Halloween Murder Mystery Dinner

Wedensday, October 20 from 7:00 p.m. - 9:00 p.m. at Beekman Arms-Delamater Inn, Rhinebck 

Join the Murder Mystery and witness the marriage of your distant cousin Frankie Alucard to Jane Dough, a mysterious girl from the mortal side of the tracks. You'll join Count Alucard, his monstrously medicated wife Elsa, and Frankie's brother Jeckyl (or is it Hyde?) as they celebrate this cursed event. Beware Renfield, the caterer to the undead, and Vampira, who spills the family’s secrets. This match made in hell has three murders. Come in costume, dance and dine, and guess whodunit! The event includes a three-course dinner and a cash bar. For more information, click here.

8. A Very Fluffy Halloween at Lilymoore Alpaca Farm 

Sat. - Sun., October 23 -24 &  Fri. - Sun., 29-31 from 10:00 a.m. to 2:00 p.m. at Lilymoore Alpaca Farm, Pleasant Valley  

Join the fluffy fun at Lilymoore Alpaca Farm for their version of a Halloween fest – only way cuter. Alpacas and goats will be in Halloween costumes, and they invite you to come dressed up too! Farm tours will be happening where you can meet furry friends and visit the Dreaming of a Chance animal sanctuary. There will be plenty of opportunities to take pictures with the alpacas in costumes. There will also be a fun workshop of wet felting soap with real fiber in great fall colors for you to take home. For more information, click here



9. Harvest Festival at Soukup Farms

Weekends in October from 11:00 a.m to 5:00 p.m. at Soukup Farms, Dover Plains 

Enjoy the crisp fall air at a farm! Soukup Farm’s annual Harvest Festival will be the first four weekends in October. Visitors can enjoy hayrides around the field leading to their Pick-Your-Own pumpkin patch where traditional orange pumpkins were grown. Then step up to a challenge and hit the corn maze. While waiting for a hayride, climb on top of the hay dragon or hop aboard a working farm tractor!  A Two by Two Zoo is also set up at the top of the upper lawn! Before the end of your trip, be sure to check out their farm store selling Soukup Farms maple syrups, and other fresh goods. For more information, click here


10. Kevin McCurdy's Haunted Mansion

Weekends in October, Fridays & Saturdays from 7:30 p.m - 11:30 p.m. and Sundays from 7:30 p.m. to 9:30 p.m. at Bowdoin Park, Wappingers Falls  

Beware of the chilling corners at Kevin McCurdy's Haunted Mansion! This year the haunted spectacular will feature "The Procedure" an indoor attraction following an evil doctor and his diabolical plans and happening on their outdoor trails, The Wicked Wood, is "Deadtime Stories". Tickets will only be available online. For more information click here

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