Things To Do in Boston This Weekend: January 23-January 25

Boston has a fun-filled week planned, setting the tone with the good food and fine wines available at the Boston Wine and Food Festival Opening Night. This weekend, experience the glitz and glamour of live performances with Dancing With The Stars: Live! The 2026 Tour. If you're looking for a good laugh, check out Learnmore Jonasi at Laugh Boston. You'll find something for everyone in Boston this weekend.

Boston Wine & Food Festival Opening Night begins the 37th annual celebration of world-class wines and gourmet cuisine at the Boston Harbor Hotel. This signature reception invites guests to enjoy a curated walk-around tasting, featuring exceptional wines from around the world paired with upscale bites from top culinary talent set against the backdrop of Boston Harbor. It's a festive, sensory start to a season of tastings, dinners, master classes, and immersive experiences designed for wine lovers and food enthusiasts alike.

Dancing With The Stars: Live! 2026 Tour will bring the excitement and artistry of Dancing With The Stars to a night of dancing at home. The show features some of the top professional dancers from the television series, presenting high-energy choreography packed with action, glamour, and entertainment. Fans will have the chance to see fan-favorite routines in person. VIP packages will be available for purchase, allowing you to interact with the tour's cast members and take photos.

Learnmore Jonasi is a Zimbabwean comedian and actor known for his keen observations, comedic timing, and captivating energy. His jokes and stories will make you laugh about the comical side of daily living, cultural differences, and misunderstandings.

This weekend's lineup captures Boston's musical range, from hushed, soul-stirring performances to high-energy hip-hop. Whether you're in a reflective, rhythmic, or refined mood, these shows offer distinct live experiences that highlight artistry, atmosphere, and connection.

Weeknights in Boston offer their unique kind of excitement. From high-stakes sports energy to creative, conversation-driven, and hands-on experiences, these events turn ordinary evenings into something worth staying out for, blending excitement, culture, and connection as the week builds momentum.