Block Island Holiday Stroll – An Annual Tradition
As the air turns crisp and the lobster pots get stacked to build the Christmas tree, the Island shifts into its favorite season of warmth and celebration. The much-anticipated Block Island Holiday Stroll—a signature event hosted by the Block Island Chamber of Commerce and Island Shops—invites guests to embrace the magic of the holidays in one of the most charming settings imaginable. It’s more than just a stroll; it’s an island-wide ritual that welcomes visitors to the quieter, cozier side of Block Island.
A Weekend of Community & Celebration
The Holiday Stroll officially sets the stage for the season, taking place in and around Old Harbor with a host of family-friendly activities. Begin with the festive spirit of the Thanksgiving Beach Walk at Fred Benson Town Beach—leashed pets welcome. Wander through vendor markets, come to the Blue Dory to try our new cookies and sip apple cider, and meet Santa at Esta’s Park for a photo the whole family will treasure. Island shops offer seasonal specials all weekend long. They also donate holiday-themed gifts for the Chamber’s curated raffle program featuring gift baskets full of local delights.
Strolling, Shopping & Island Charm
Make your way along the centrally-located streets—Dodge, Water, Chapel, Corn Neck Road—where participating shops, galleries, and restaurants participate in the stroll. Each location offers stamps for the raffle sheet: visit all and earn your chance to win one of the festive gift baskets. Admire handcrafted ornaments, locally-designed apparel, and artisan pottery while the smell of fresh cookies and cider drifts through the air. The walk isn’t just about seeing it all—it’s about immersing yourself in island tradition and the holiday spirit in a beautifully relaxed setting.
Food, Music & Festive Fun
The Holiday Stroll weekend offers far more than shopping. Hot soups and grilled cheese fundraisers, DJ nights at Yellow Kittens, or a ghost tour with Block Island Ghost Tours adds to the experience. Whether it’s the ukulele carols, the marketplace at the library, or the glowing lights at dusk, the soundtrack of the weekend is unmistakably joyful and unmistakably Block Island. To get all the details, be sure to check out the Block Island Chamber of Commerce website. You can see the complete guide for all shops, restaurants. and activities available throughout the weekend here.
Extend Your Stay, Enhance the Magic
Why hurry away after the stroll when you can linger and enjoy a full Island experience? Extend your stay at two of the finest inns on Block Island—Avonlea and Blue Dory Inn—both located within easy reach of all the festivities.
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At Avonlea, you’ll wake to the rhythmic rush of the waves, enjoy gourmet breakfast, and settle in by the fire after a day of strolling.
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At Blue Dory Inn, enjoy a welcoming hearth, warm cookies, and comfortable ocean-view rooms that keep you just steps from the fun.
Both inns put you at the heart of Old Harbor’s cheerful energy while offering tranquil retreats when you’re ready to slow down. Friday nights are limited but there are many options for Saturday or Sunday stays.
Be sure to take a close look at the ferry schedule. The only departure location is from Pt. Judith in Narragansett, RI. The Block Island Ferry runs the hi-speed ferry in addition to the traditional ferry for the Block Island Holiday Stroll only.
Why the Block Island Holiday Stroll Is the Perfect Time to Visit
In the bustle of summer, Block Island sparkles, but in this seasonal pause, the Island shines in a more intimate light. The Holiday Stroll is your invitation to experience local hospitality and the charm of a seaside town dressed in winter’s best. Stroll, shop, sip, and stay awhile—you’ll find the magic of the holidays wrapped in local joy and coastal beauty.
Join us this year for the Block Island Holiday Stroll—where tradition meets sea breeze and every moment feels infinitely memorable.
Book online at blockislandinns.com or call us at 401-466-5891 to book a room at the Blue Dory or Avonlea.
