51st Annual Nantucket Holiday Stroll Weekend

The 51st Annual Nantucket Stroll will take place from Friday, December 5 through Sunday, December 7, 2025. This year’s theme, “Shine On, Nantucket,” celebrates the theme of resilience, unity, and spirit which truly make the island community glow, especially during the holiday season. Festivities include Santa’s traditional arrival via his nautical “sleigh” at noon on Saturday followed by a full line up of activities, including roaming carolers in Victorian garb, the Magical Talking Tree, craft shows, a European-style Christmas Marketplace, and more.

Nantucket's boutiques and restaurants will celebrate Stroll Weekend with special sales, promotions, and holiday cheer. For a listing of shops, restaurants, and accommodations, visit ShopNantucketIsland.com.

Stroll Weekend highlights include:

ASHA - 18C Federal Street

bar Yoshi and O bar - 21, 7-8 Old South Wharf

Bodega - 2 Candle Street

DAWN - 2 Harbor Square

Ellsworth & Ivey - 34 Main Street

Haul Over - 7 Salem Street

Hepburn - 3 Salem Street

Love Shack - 10 Old South Wharf

Nantucket Boat Basin Authentic Shop - 33 Straight Wharf

Sara Campbell - 5 South Beach Street

Summer Shades - The Courtyard at 16 Straight Wharf

The Black Dog - 40 Straight Wharf

The Skinny Dip - 23 Old South Wharf

vineyard vines - 2 Straight Wharf

NIR Retail

NIR Retail, a New England Development company, leases 100 of Nantucket’s premier retail locations found on Nantucket’s most popular shopping streets: Main, Centre, Federal, South Beach and South Water, and on Old South Wharf and Straight Wharf. Shops and galleries include Veronica Beard, Southern Tide Nantucket, Skinny Dip Nantucket, Cavalier Ebanks Gallery, Brown Basket Gallery, vineyard vines Nantucket, and more. Favorite Island restaurants include CRU, Lola 41, Ventuno, The Nantucket Tap Room, The Gaslight Nantucket, and more. Located off the coast of Massachusetts, Nantucket has welcomed generations of visitors and residents. Its world-class shops, restaurants, hotels, and seaside beauty have made Nantucket one of the most popular resort destinations for vacationers from around the globe. Visit ShopNantucketIsland.com for a full listing of galleries, shops and restaurants.