As the spooky season nears, you may find yourselves pondering the idea of a fall vacation. For families with children, many schools are online now, and many more are offering fall breaks, making it easier to slip away during this wonderful time of the year and for those who work from home, the home in question doesn’t have to be your home, it can be located anywhere in the world. Like on Cape Cod, for instance, where the cool weather will hint at winter, the full moon will take on a spooky vibe while glinting off the ocean waters, and the stores, homes, and restaurants will be decorated for the holiday! Offering all the things you can expect to do at this time of year, including harvest festivals, trick-or-treating, and maybe even a pub crawl or two, ensuring that this Halloween will be memorable, especially when you choose one of our New England Vacation Rentals holiday hideaways to relax and recuperate in at the end of every day! This guide to your escape to the Cape will bring you thrills, chills, and a spooktacular time.


The first words out of your children’s mouths when you told them about this Halloween adventure on Cape Cod more than likely involved costumes and trick-or-treating, and we can reassure you that they will be able to enjoy both. Trick-or-treating in the various communities on Cape Cod is safe and fun, and as you walk in the footsteps of trick-or-treaters that have followed these same paths for centuries, you won’t help but be charmed by the beauty of the architecture and the creativity of the decorations. Trunk-or-Treating is also a popular Halloween event, giving the kiddos the opportunity to beg for treats in a safe and contained environment and may be offered in many of the towns and villages of the Cape. Parents aren’t always comfortable letting their children run mild in new environments, and this could be an easy solution. Halloween is celebrated on October 31st for general trick-or-treating, but trunk-or-treating could be held earlier, depending on the town in which you are staying.

Haunted Houses

To experience Halloween to its full extent, a visit to a haunted house should definitely be added to your holiday itinerary, and the Cape offers more than a few for your spine-tingling enjoyment! Every year is different, of course, but towns such as Brewster, Harwich, and Orleans have previously offered haunted houses so frightening, it is recommended that your tiniest travelers not participate. Orleans has also provided a Haunted House Kid Friendly Stroll in past years, allowing traveling families the opportunity to celebrate and explore without inducing nightmares for the littles.

Fall and Halloween Festivals

A seasonal festival brings us some of life’s greatest pleasures and in the waning days of fall, there will be more than a few you should plan on attending! Pumpkin People in the Park, generally held in mid-October through the end of the month in Chatham, is one event we always plan on attending, especially since Chatham has been listed as the 4th in America for being the best Halloween Town by Travel & Leisure magazine, and this cool festival is one of the main reasons. Explore the creativity of our locals as you stroll through Kate Gould Park, counting and photographing all of the pumpkin people that are residing there, all in costumes and using pumpkins as their heads. This wonderful festival also coincides with the town’s Oktoberfest celebration, so be sure to enjoy an ice-cold brew while there. Oktoberfest is celebrated in other Cape Cod towns, including Dennis, so be sure and check out where the parties are happening if this is something that appeals to you! As we get closer to the winter months, however, there won’t be as many festivals as there are in the summertime, so be sure and plan a second visit during the summer solstice. Our homes are equally luxurious and welcoming in the summer months as well!

Barnstable Village Haunted & History Tour (Reservations Required, (508) 241-1151)

Sometimes the spookiest activities can be the ones with roots firmly embedded in reality, and the Barnstable Village Haunted & History Tour is the perfect example. Offering a peek into the history of Cape Cod while also taking guests on a two-hour tour of where restless spirits may roam, the tour ends in the oldest wooden jail in the nation, one that was built in the late 17th century, where unhappy spirits make their presence known on a regular basis! Also taking tourists through Cobbs Hill Cemetery, this chilling adventure may be the one you remember the most. Bring your cameras and your bravest attitude and spend a couple of hours on historic Cape Cod getting to know the spookier side at Halloween!

Time to Dine

We don’t know why it is, but the cool weather at Halloween makes our appetites grow larger, and if you are interested in more than pumpkin spice lattes and muffins, (Snowy Owl Coffee Roasters, 4 Merchants Road in Sandwich is one of our favorite coffee spots, FYI.) there are plenty of restaurants on Cape Cod that will serve hearty meals that stick to your ribs. One of our absolute favorite comfort food spots, Captain Scott’s Seafood Restaurant, can also be found in Sandwich. Located at 71 Tupper Road and offering a seafood-centric menu so sweet and rich, you may want to visit at lunch AND dinner to ensure you get your fair share of the best comfort food on the Cape! For our Chatham guests, you may want to stop in at Chatham Moods Café & Grill, located at 1617 Main Street and featuring a breakfast, lunch, and weekend brunch menu that will make you feel warm, cozy, and well-fed! Breakfast is the most important meal of the day, according to the dieticians and doctors, and the breakfasts served at Good Friends Café, 83 School Street in West Dennis, may become a tradition during your stay! Serving all your breakfast favorites, their light and fluffy pancakes are nearly the size of the dinner plates upon which they rest, and we dare you to leave this delicious downhome restaurant still feeling hungry. (Trust us, it can’t be done!)

Celebrate the Holiday with New England Vacation Rentals

Of course, the best part of your Halloween scare-ventures may be enjoyed at home in your holiday hideaways we at New England Vacation Rentals offer for our guests! Watching a horror movie marathon on state-of-the-art televisions, creating spooky feasts and spine-chilling beverages in our fully equipped kitchens, and experiencing long nights of peaceful sleep with only happy dreams interrupting your REM sleep! Nightmares are forbidden in our beautiful homes, and when you wake up every morning feeling recharged and ready to face a new day of Massachusetts adventures, you will know that you made the right decision when you chose New England Vacation Rentals for your vacation escape. Reserve your favorite today and explore all the holiday activities we listed above plus even more!

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