Small-town Halloween Fun in Sag Harbor
Sag Harbor is a small town on the east end of Long Island, a two-hour drive from New York City. It’s part of the area known as the Hamptons, a famous resort area known for its beauty, beaches and history of artist residents such as Jackson Pollock, as well as plenty of current celebrity residents. Despite this glamorous reputation, there are plenty of small-town annual Halloween activities in Sag Harbor, for kids and families. From pumpkin picking to costume parades, homemade cider and donuts, here are a few of the annual Halloween activities you can enjoy in Sag Harbor, New York.
First, you’ll want to pick a pumpkin. There are a number of u-pick patches in this region, but a special favorite is the Milk Pail farm. They have a vast patch of on-the-vine and pre-picked pumpkins including giant pumpkins, a variety of small multi-colored gourds, cooking pumpkins and medium-sized pumpkins perfect for carving jack-o-laterns with carving tools you can buy in downtown Sag Harbor at the hardware store or the 5&10 Variety Store. When you’ve loaded a wheelbarrow with the pumpkins of your choice, you can purchase your items along with some of the Milk Pail’s special homemade cider and donuts.
Another great farm activity is corn mazes, of which there are several in this area. This is a really fun, special seasonal activity. A corn maze is where a field of corn grows around a twisting path. The corn is planted in Spring, than the path is mowed once it has reached a medium height, and spray is applied to the path to keep it from growing over, and the corn grows high walls around it. Corn mazes are like hedge mazes, which are a long-standing tradition that became popular in 15th century Europe, especially England.
One of the funnest annual Halloween activities in Sag Harbor is the Children’s Halloween Ragamuffin parade on October 28, a long-standing tradition. Kids of all ages, from toddlers to teens and even many adults, march down Main Street in a variety of adorable and frightening costumes, ending at the historical Customs house. From elaborate homemade creations to store-bought costumes from the 5&10 or the Ideal, nothing says Halloween like this colorful parade, and it’s even more fun to participate in. After the parade the kids can partake in the Pumpkin Trail, where they can trick-or-treat in stores that display the Sag Harbor Chamber of Commerce pumpkin their window, on Main Street and beyond. It’s a lot of fun to explore Sag Harbor’s stores this way – by collecting candy! There is also a Sag Harbor School Halloween Parade on the 27th, and costume contests take place in various places.
If you and your children would like to participate by getting Halloween costumes for yourself, the 5&10 Variety Store has a wide selection of pre-made, full-body kids and adults costumes, masks and accessories. There you can find what you need to dress up as an animal, a pirate, a ghost, a cartoon character or any variety of other characters. You can put together accessories to invent your own character, or visit the crafts section for supplies to sew your own. There are many types of cloth, thread, ribbon, yarn and craft supplies in the left side of the store for the more ambitious Halloween costumers.
And of course, there is the trick-or-treating. This activity usually starts fairly early in the evening, around 4 or 5pm. It’s especially nice to trick-or-treat in a small community like this, as there are lots of houses nearby and they are all friendly. Some houses have elaborate decorations and sound effects, and there are a couple houses specially known for their generous goodie bags, one of which always has a grand display of twenty or thirty jack-o-lantern Pumpkins in their front yard!