N Magazine’s insider guide to Columbus Day Weekend.

Everyone knows that Memorial Day Weekend, Fourth of July, and Labor Day Weekend are fun-filled times on Nantucket, but did you know that Columbus Day Weekend is secretly one of the best times of the year? With the leaves changing and warm weather still in the air, the first weekend of October is primed for a good time. Read on for our top tips on everything happening this holiday weekend.


Good Eats and Parting Treats – Restaurant Closings
All good things must come to an end, and even our favorite popular restaurants must take a breather for the winter season. Take advantage of the sales and closing parties this Columbus Day Weekend, and make sure to spread out your meals as much as possible. We’ve done the calendar searching for you – Jetties Sandbar, The Pearl, Boarding House, Millie’s and Chanticleer will all close up Sunday, October 7th (extra pro tip: Sandbar is hosting a rockstar themed party from 11:30 am – 8:00 pm that day, and The Pearl and Boarding House will have a “Last Call Wine List” with slashed prices.) On Monday, start your day off with a coffee and a breakfast sandwich at Provisions, as they will close when they run out of bread. Then head to CRU for their Studio 54 themed brunch bash in the afternoon (sequin and dancing outfits are a MUST). Close out the holiday with Straight Wharfs 1/2 off menu for dinner and their famous “86 SWR” party in the evening.


Get Active in Autumn
Columbus Day Weekend marks the true beginning of fall on Nantucket, and the perfect way to enjoy the gorgeous changing foliage is to participate in the 8th Annual Nantucket Half Marathon on Sunday at 8:00 am. With the route traveling through wooded dirt roads, tree-lined bike paths and ocean view avenues, this half marathon is one of the most scenic on the East Coast and gives the opportunity to see parts of the island you never knew existed. If 13.1 miles seems like a bit much, check out our runner’s guide to Nantucket for a shorter and more relaxing route.


Engage Your Inner Artist
If you prefer to spend your weekend immersed in culture rather than calisthenics, check out the Manhattan Short Film Fest on Friday night from 7:00 – 9:15 pm at the Atheneum, before attending the Nantucket Shorts Film Festival on Saturday from 4:00 – 6:00 pm. The fifth annual Shorts Fest brings together filmmakers, screenwriters, and actors from around the island to produce cinematic masterpieces under 10 minutes long. If live theater is more your thing, take in a performance of the Theatre Workshop of Nantucket’s The Cocktail Hour, White Heron Theatre‘s one-man-show Fear of Heights, or The Dreamland‘s production of the Diary of Anne Frank.


Explore the Island Environment
On Saturday, get out and about early and head to Sankaty Head Lighthouse, where the ‘Sconset Trust will be opening the famous landmark for tours. Wear your sneakers for the climb to the top but leave the drove at home – you’ll get a better scenic view of the island than even your best camera could capture. Then head off to Milestone Cranberry Bog for the Nantucket Conservation Foundation’s 2018 Cranberry Festival. This event is perfect for the whole fam, and you can even bring the dog too! Those who come out will be able to watch a cranberry harvest, learn about the history of cranberry farming on Nantucket, participate in family activities, or just kick back and enjoy the music and scenery of one of the most unique places on island.


Fulfill Your Fall Instagram Dreams
Leaf peeping isn’t just for Vermont and New Hampshire – you can find some of the best autumnal views right here on island. Grab your friends and take a few pics in the Serengeti pastures along Milestone Road, in the trees in Nantucket State Forest, or out by Sesachacha Pond. Looking for more iconic Nantucket backdrops? Brant Point, Main Street, and ‘Sconset are still beautiful and clear of tourists this time of year. Or for the ultimate picturesque fall moment, put on your warmest sweater, pack some firewood, and hit the beach for an evening bonfire with the whole family. Cozy up with hot chocolate and s’mores, and remember to bring beach chairs, bug repellent, and plenty of blankets. Who knows, you may even have such a nice time enjoying Columbus Day Weekend that you forget to take the Instagram after all.

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