NANTUCKET, MASSACHUSETTS (Holiday 2025) – 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
Enjoy 20% off storewide during our Special Stroll Sale (excluding the new holiday collection) and be the first to shop their exclusive hand-beaded, 1960s island-inspired holiday capsule of clothing and jewelry. Shoppers can also enjoy sips and sweets, plus receive a custom Tuck Shop x Asha chocolate bar with purchases over $250.
bar Yoshi and O bar
21, 7-8 Old South Wharf
bar Yoshi and O bar will be open for Stroll weekend from 10:30 a.m.-10:00 p.m.(kitchen hours) and until last call for the bar featuring food and cocktail specials, and a pop-up shop outside with handcrafted holiday gifts.
Bodega
2 Candle Street
Open 10:00 a.m. to 5:00 p.m. for Stroll and every day. The shop is fully decorated with themed trees and displaying an exclusive Nantucket 2025 ornament. The boutique is chocked full of a selection of sweaters, mittens, handbags, and best-selling Enewton jewelry.
DAWN
2 Harbor Square
Open daily Stroll weekend, from 9:00 a.m. to 7:00 p.m. with sales running from 30%-60% off. Sips and sweets will also be provided throughout the weekend.
Ellsworth & Ivey
34 Main Street
Open during Stroll weekend from 10:00 a.m. to 6:00 p.m., with a special sale of up to 50% off merchandise.
Haul Over
7 Salem Street
Special Stroll engraved Yeti Tumblers will be available in three styles. Store is open all week long, Monday through Saturday 10:00 a.m. to 6:00 p.m. and Sunday 10:00 a.m. to 5:00 p.m.
Hepburn
3 Salem Street
Hepburn’s local jewelry designer Lynn Symons will be in store showing her beautiful jewelry daily. Many sale items and specials, and more.
Love Shack
10 Old South Wharf
Open Friday & Saturday of Stroll weekend from 10:00 a.m. to 5:00 p.m. The entire store (excluding gift cards) will be 20% off, with a curated collection of sale items.
Nantucket Boat Basin Authentic Shop
33 Straight Wharf
Stroll wearables include 2026 Authentic Scarf and drink ware. All Non Stroll merchandise will be 50% off. Store hours will be Thursday from 9:00 a.m. to 6:00 p.m., Friday and Saturday 9:00 a.m. to 9:00 p.m., Sunday from 9:00 a.m. to 6:00 p.m. and Monday from 9:00 a.m. to 5:00 p.m.
Sara Campbell
5 South Beach Street
Open all Stroll weekend, Thursday through Sunday, from 10:00 a.m. to 5:00 p.m. daily. 20% off full price apparel and an additional 50% off sale merchandise.
Summer Shades
The Courtyard at 16 Straight Wharf
60% off all sale styles for Stroll Saturday and special gift with purchase on Chanel, Costa, Maui, SALT & Smith brands.
The Black Dog
40 Straight Wharf
Save 15% off the entire store and customers receive a free canvas tote bag with their purchase of $125 or more. Look for special Stroll merchandise available in store and at the Holiday Market on Saturday.
The Skinny Dip
23 Old South Wharf
Stroll sale featuring up to 70% off.
vineyard vines
2 Straight Wharf
Nantucket Christmas Ornament gift with purchase ($250 or more, while supplies last).
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.
New England Development
For over 50 years, New England Development has taken a creative, entrepreneurial approach to real estate development and management, delivering, and sustaining successful projects across a wide range of property types. The company’s national portfolio includes mixed-use developments that combine retail, residential, office, lab and hotel use, outlet centers, high-end and street-front retail, airport retail, hotels, golf courses, restaurants, and marinas.
New England Development’s diverse portfolio includes CambridgeSide in Cambridge, MA, Chestnut Hill Square in Chestnut Hill, MA, Outlets of Des Moines in Altoona, IA, Clarksburg Premium Outlets in Clarksburg, MD, Newburyport Development and Marinas, Nantucket Island Retail and The White Elephant Resorts, among others. For more information, visit NEDevelopment.com.