10 Ways to Enjoy the Weekend on Long Island Without Packing a Suitcase (or Losing Your Mind)

If you’re like most families on Long Island, that post‑Thanksgiving stretch from Friday to Sunday is a delicate dance. You're full of turkey, your kids are buzzing on leftover pie and candy canes, and you're already dodging the holiday chaos like a professional goalie.

So instead of stress-scrolling through Zillow listings or trying to squeeze in one more Black Friday deal, let’s talk about something better: getting out of the house, doing something fun, and maybe even making a few memories you won’t need a therapist to unpack.

Here’s how to spend the weekend of November 28–30 around Long Island with a mix of family-friendly fun, festive vibes, and maybe — just maybe — a moment to catch your breath.


Friday: Start slow… or skate fast

If your kids are bouncing off the walls, United Skates of America in Seaford has a public skating event on Friday featuring none other than... Stitch. Yes, that Stitch. Skating + kids + Disney character = a full night’s sleep later. You’re welcome. Bonus: It’s indoors, so you can ignore whatever cold front is creeping in.

If skating isn’t your thing (we get it — ankles are fragile after 40), head over to the Long Island Explorium in Port Jefferson for Community Appreciation Day. It's interactive, educational, and just geeky enough that your kids think they’re playing while you secretly call it learning. And hey — it’s a great chance to sneak in a hot chocolate while they tinker.


Saturday: Lights, and truffle dreams

Saturday evening is prime time for the Huntington Holiday Parade & Spectacular. Floats, lights, live music, and tree lighting that will make even the most cynical New Yorker mumble, “Alright, that’s kinda nice.” Bring the kids, bundle up, and get ready for the ultimate Long Island version of Hallmark holiday vibes.

Feeling festive... but also fancy? Wine lovers (and tired parents) might want to sneak away to Sparkling Pointe in Southold for their “Eat, Drink & Be Sparkling” truffle tasting. Sparkling wine, winter truffles, and adults-only conversation. This one’s less “bring the kids” and more “text the sitter.”


Sunday: Markets, crafts, and one big brunch

By Sunday, you might want something relaxed — or maybe a chance to pick up a few holiday gifts without elbowing someone over a PlayStation at Target. Enter: the Holiday Night Market Wonderland at the Reboli Center in Stony Brook. It’s got a heated tent, outdoor village, holiday treats, and even snowfall. (Okay, it’s fake snow... but the kids don’t care, and you didn’t have to shovel it.)

Or if you’re looking for something a little different, head to RGNY Winery on the North Fork for “Brunch a la Mexicana.” It's family‑friendly, has great food, and if you’ve never had huevos rancheros with a wine pairing, trust me — you’re overdue.

Still got energy? Swing by the Huntington Holiday Market on Wall Street to round out your weekend with a little more local love. Great for finding gifts, grabbing hot cider, or just strolling with your spouse while the kids hunt for cookies and crafts.

Bonus Round: Keep these in your back pocket

  • Country Parlor Folk Art Show in Riverhead for charming gifts and homemade goodness.

  • Broadway Mall Christmas Vendor Fair if you want a simple, no-fuss indoor market.

  • Planting Fields Arboretum Holiday Market for nature + shopping = holiday harmony.


Final Thought:

Whether you’re looking to skate, sip, shop, or just survive, Long Island’s got a full plate of events this weekend that don’t require a plane ticket — just a little planning and maybe a travel mug of coffee.

And if you’re also thinking, “Should we upsize next year?” — let’s talk. My job is to help you find your next great home, without adding stress to your holidays. But first? Go out, enjoy Long Island this weekend... and leave the Zillow app closed until Monday.