Why: The 47th annual Christmas Stroll, November 28 – December 6, 2020 feels like you’re stepping into a Charles Dickens backdrop with every corner of Nantucket’s historic downtown transformed into a winter wonderland. As an ode to its original roots, the theme of this year’s event will be centered around shopping local for the holidays. Stroll originally started over 40 years ago as an effort to keep residents from leaving Nantucket to buy gifts on the mainland. Today, boutiques remain open through early December and have elaborately designed storefronts outfitted with twinkling lights. Downtown is also dotted with hundreds of seven-foot fit lit trees decorated by locals that line the cobblestone streets. Festive attire and ugly sweaters are encouraged. Spend the holidays at the White Elephant with multi-bedroom accommodations large enough for the whole family.
How: Cape Air flights connecting from Boston are available to the island year-round, as is the ferry service from Hyannis, MA.
Rules: All visitors and returning residents are required to complete a Massachusetts Traveler Form unless they are coming from a state that has been designated a lower risk COVID-19 state. The new travel order notes that visitors and returning residents arriving in Massachusetts from any place other than a COVID-19 lower-risk state must quarantine for 14-days unless they can produce a negative COVID-19 test. The current list of lower risk states who are exempt from this travel order: Connecticut; Hawaii; Maine, New Hampshire; New Jersey; New York; Rhode Island and Vermont.