October is probably my favorite month of the year. Ok, Ok, maybe November is too, but October is a very special time in the Hudson Valley. With so much to do and so much to see, it is hard keep up with al that's going on. It is often difficult to narrow down the Best Places to Visit in the Hudson Valley any time of the year. October, though, seems the most difficult month out of all of them.

Looking for something to do in October? Here are the best places to visit in the Hudson Valley in the month of October.


As everyone starts to get ready for all things 'Halloween', the Hudson Valley shows off its Autumn flair and colors. In addition to the Scary and Haunting things to do, the Hudson Valley is also full of non-Halloween festivals and Autumn celebrations.

Although Autumn and Fall Activities take place through November, I am here to show you the activities that you should not miss in the month of October.

Take out a piece of paper and pen and start jotting down some these Special Events. Make sure you go to one or some this year!


According to the I Love NY Website:

"From spooky fright fests and Halloween parades to film festivals and food, you’ll soon realize why fall is the best time to travel to the Empire State."


Best Places to Visit in Westchester County

Sleepy Hollow and Tarrytown are some of the most famous places to visit during the Halloween Season.

Situated along the Hudson River, Sleepy Hollow is the setting of Washington Irving's, "The Legend of Sleepy Hollow". That alone makes it the most popular Hudson Valley Destination in October.

Below are just some of the events that take place in the area in honor of the famous tale.

  • Sleepy Hollow Cemetery Tours - Not sure if this is sort of your thing, but this is something I would love to do! Any History lover or admirer of stone statues would love this tour. They offer several different tours during the season.
  • Horseman's Hollow at Philipsburg Manor - During the month of October, Philipsburg Manor is transformed into an interactive and terrifying scene. And immersed in "Legend of Sleepy Hollow".
  • Irving's LegendWell if Horseman's Hollow doesn't scare you enough, why not try Irving's Legend at the Old Dutch Church.

Another popular event in Westchester County is the Great Jack O' Lantern Blaze. This yearly event takes place in Croton-on-Hudson at Van Cortlandt Manor and is truly NOT to be missed!

October is the best time to visit the Hudson Valley. The best places to visit in the Hudson Valley are featured in this post.

Down the road from Tarrytown, Lyndhurst Mansion hosts 'Jay Ghoul's House of Curiosities'. Also in Tarrytown, you can visit the home of Washington Irving -  Sunnyside: Home of 'The Legend'.

If Harvest Festivals are more your speed, then make sure you visit several in the Westchester County area. These are some popular ones:

Best Places to Visit in Rockland County

The following Festivals can be found in Rockland County:

Bear Mountain State Park hosts their Annual Oktoberfest.

Best Places to Visit in Orange County

October is the start of Autumn in the Hudson Valley. Pumpkin picking is the favorite activity every October.

Best Places to Visit in Dutchess County


Related Post:

Although Fall Festivals are lots of fun, remember that many of the local Hudson Valley Farmers Markets continue to be open during the month of October.


Best Places to Visit in Ulster County


In Conclusion

No matter where you decide to drive to or which activity or festival you decide to partake in, The Hudson Valley shows off its Beauty, Mystery and sense of Community each year in the Month of October.


Which is your favorite festival or Activity in the Hudson Valley?

A Few Things to Know Before attending these events: 

  • Many of these events and festivals are ticketed. Popular events, like the Great Jack 'o Lantern Blaze usually sell out quickly.
  • Many of these events are rain or shine, although some do offer Rain Dates.
  •  Check each site for updated information.

Until the Next Adventure...

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Here is a list of the Top & Best Places to Visit in the Hudson Valley during the month of October.

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