It’s that magical time of year and these holiday strolls, from the North End to Nantucket, led by some of Boston’s most vibrant social influencers will be sure to guide you through this gift-giving holiday season. Happy gifting!
Kick-off the holidays with the North End’s 10th Annual Holiday Stroll on December 2 from 6-11 p.m. Local stores include LIT Boutique, Salmagundi, Injeanius, Shake the Tree, Polcari’s Coffee and more will stay open late and feature special offers. Join bloggers Kristen Uekermann, Daena Jeanne, Alyssa Stevens, Matthew Simko, and Elissa Garza in exploring the narrow streets, trendy boutiques, wine stores, and specialty shops. Pick up a shopping passport at any of the participating stores and get it stamped at all 15 locations to be entered to win the exclusive gift package filled with products provided by each business. Share your moments on social media and join the conversation with #NorthEndHolidayStroll as they takeover Only In Boston Snapchat at 8 p.m.
Attend the 8th Annual Holiday Shopping Night on December 7 from 4-9 p.m. The festive evening will include special promotions and celebrate at over 20 neighborhood shops and area restaurants. A special thank you to event sponsors Washington Gateway Main Street, South End Business Alliance, GTI Properties, and Siena Condos at Ink Block. Guests can expect free parking with free pedi-cabs from 5-8 p.m. providing transportation from the parking lot to the South End’s shops.
The Beacon Hill Holiday Stroll is taking place on December 8 starting at 3:30 p.m. for pictures with Santa Claus at Hill House firehouse. Holiday shoppers can visit stores like Follain, Crush Boutique, KMHudson Ltd., and more boutiques offering special deals. The festive night will include the Christmas tree lighting, carolers, and horse drawn carriage rides, and throughout the evening guests will enjoy performances by the Apollo Club Men's Singing Group, Back Bay Bell Ringers, King's Chapel Choir, and Brass Quartet.
Enjoy a stroll weekend on Nantucket from December 2-4 with influencer Holly Finigan of Nantucket blACKbook as you shop her new Happy Place holiday collection featuring limited-edition T-shirts, holiday red hoodies, baby onesies, and more. Stay at the recently-opened Greydon House and sip cocktails by Boston’s award-winning bartender Jackson Cannon next to the fireplace after shopping Nantucket's charming boutiques like Blue Beetle, Town Pool, The Skinny Dip, and Epernay Wine & Spirits. Then, visit the Nantucket Whaling Museum to glimpse the more than 80 decadently trimmed trees during the Festival of Trees. Close out the weekend with Sunday brunch and live music by PJ Moody at Brant Point Grill.
The Fort Point Holiday Stroll is celebrating its annual event on December 16 from 4-8 p.m., stroll through the historic neighborhood, nibble sweet and savory treats from restaurants and bars, explore galleries, artist studios, and shop at boutiques including some special pop-up shops. Don’t forget to grab your map at any of the participating locations, explore the neighborhood, and collect stamps for a chance to win amazing prizes from local boutiques and restaurants.