Traveling at Halloween is something not everyone can do, but if you are one of the lucky few, completing a journey to Cape Cod may just end up being your new favorite way to celebrate the holiday. The crowds lessen during this amazing time of year, giving visitors more opportunities to live like a local, which of course means celebrating Halloween. Participate in local trick or treating, attend Halloween events, and because your comfort matters, come home every night to one of our Pretty Picky Properties to relax and savor a holiday that appeals to the quirky rebel that lives on inside most travelers! Our guide to spending Halloween on Cape Cod will give you, your family, and/or your best friends who are traveling with you, a way to enjoy everything that makes the holiday the most spooktacular time of the year!

Dennis Halloweenpalooza, October 28th, Johnny Kelly Field 

There really is a lot going on this Halloween on Cape Cod, so hopefully we can manage to get it all in! October 28th, the Dennis Halloweenpalooza celebrates everything spooky with this festival of fun! Offering a Kid Candy Haunt that starts at 2 pm and a Cornhole Tournament with cash prizes for the winners, this event is designed for both adults and children to enjoy! And because the Kid Candy Haunt takes place on the 28th and the Dennis community will be celebrating trick or treating on all Hallow’s Eve, your kiddos have twice the opportunities to get the good candies you will be sneaking from their bags after they fall asleep!

Crosby Halloween Spooktacular Show, October 26th-28th, Crosby Mansion in Brewster 

This family-friendly event offers fun and fancy in the classic surrounds of the Crosby Mansion, constructed in 1888 and serving as a Brewster Museum today. Offering a show filled with magic, charm, mystery, and everything Halloween, your kiddos will be thrilled to experience a sneak peek of the big day! Also in Brewster, on October 27th the Brewster Recreational Department is putting on a Halloween Parade beginning at the Brewster Ladies Library at 10 am and your kiddos are invited to don their costumes and join in the parade! Finally, as throughout the Cape, trick or treating will be held on October 31st, ensuring that the holiday fun will last over a few days! 

Pumpkin People in the Park, October 14th-31st, Kate Gould Park in Chatham 

This fun annual event is open for viewing every day of the week the last two weeks in October and is Chatham’s whimsical way of celebrating the holiday! Throughout the park, various merchants put displays of pumpkin people. Featuring cloth bodies and pumpkin heads, a walk in the park takes on new meaning as you pose for selfies alongside your favorite creations! The Trick or Treat Treasure Hunt & Bonfire Boo Bash is a child themed Halloween event taking place at 297 Shore Road on October 28th, featuring games, treats, and costume contests for the littles, and of course, trick or treating takes place on Halloween in most Chatham neighborhoods! 

Barnstable Village Haunted & History Tour, US Coast Guard Heritage Museum in Barnstable 

If you really like to be scared, this haunted tour helps you understand a little bit more about the history of the area while bringing participants to the spots where the curtain between us and the spirit world is thinnest! Stopping in over 10 of the most haunted spots in town, including the Cobb’s Hill Cemetery and the Old Jail it has become a local tradition for Halloween visitors. Trick or Treating takes place on the holiday itself, so don’t forget to bring costumes for the kids, or, if you want to save room in your suitcase for souvenirs, there is a Halloween Spirit store open in town, located at 790 MA-132, offering a huge selection of costumes cute, sweet, and scary! 

No Scares with your Pretty Picky Properties Holiday Hideaways!

As much as we appreciate the raising of goosebumps on our arms and the jump scares that take place in our favorite Halloween movies, no one wants to live in a haunted house, not even when it is just for a week’s vacation. Fortunately, we can promise that although you can watch an unlimited selection of scary movies on smart or cable access televisions and you will be able to create all the holiday treats you want in fully equipped kitchens, there will be nothing that scares you off the screen when you choose Pretty Picky Properties! Sleep dreamlessly in premium beds, gather round roaring fires with mugs of mulled wine on chilly nights, and wake up every morning ready to enjoy new Halloween adventures on Cape Cod! Reserve your favorite Halloween rental today and experience a holiday you will never forget!