SOR’s guide to a fall weekend in nantucket


Nantucket is a small island that resides of the coast of Cape Cod, Massachusetts. It was discovered and incorporated in the 17th century and served as a whaling hub. Since it’s redevelopment in the 1950s, it is now the premier summertime destination for the perennially preppy.

Since the island in its entirety is protected as a historical district, all residential and commercial areas adhere to strict building codes, protecting the colonial east coast appearance islandwide. This gives Nantucket its fairy tale charm.

I was lucky enough to spend this past Columbus Day Weekend on island. I have been to Nantucket a few times prior, but always during the summer months. Nantucket’s most attractive season is summer, but it was exciting to experience the island in October.

Below, I’m sharing some of my favorite autumnal Nantucket experiences to take with you on your next trip.

Getting There

Since this is the offseason, travel and lodging tends to be much cheaper. You can fly directly onto the island from New York or Boston via Cape Air, or take a bus to Hyannis and a ferry to Nantucket for a cheaper option. October is wedding season there, so as always, be sure to book travel in advance.


IMG_6691The Vanessa Noel Hotel, proprietered by the shoe designer of the same name, is right in the middle of town.

If you’re traveling alone, the Carlisle House Hotel is also a short walk to town and features some communal areas for meeting other Nantucket-goers.

Eat & Drink

For breakfast, head to Fog Island Café, a fail-safe greasy spoon with cheap good eats, right near the water. Or, grab a coffee from artisan roasters The Bean.


If you seek to get out of town for a spell, take the bus to Cisco Brewers to try some local craft ales.

Dinner options are endless, but from my latest trip, I will recommend The Met on Main or Ventuno. Fresh seafood is still fair game come harvest time – fall is actually scallop season (if interested, you can go harvest your own on the beach).

My absolute favorite restaurant is straight wharf – and yes, I got the scallops.



Current Vintage had always charmed me with its selection of elegant vintage clothing, but they recently have moved into retailing wine as well, giving me more and more reasons to keep coming back.

Townpool’s new location on Main St still boasts an eclectic selection of preppy attire (think, American flag print blazers for men), but the real treat is in their basement with an inexpensive candy store and a ‘zero-gravity’ room for your next Instagram.



I came to Nantucket on Columbus Day Weekend to run their half marathon, but if that’s not your speed (no pun intended), check out the cranberry festival & bogs on Saturday of that same weekend.

A new art gallery with generous windows has opened up at 14 Easy Street, right across the street from the boat basin in town. No matter which way you’re looking, you’ll be seeing something lovely.

Nantucket’s history and preservation of the original buildings means the town offers an array of ghost tours, the perfect activity to do on a chilly October evening to set the mood for Halloween.

Follow me on Instagram @serialoutfitrepeater.

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