As the holiday season approaches and Boston’s historic streets begin to shimmer with festive light, your stay at Clarendon Square Inn offers more than luxury—it is your gateway to a collection of events, dining, culture and seasonal flair. Below are ten standout happenings from Thursday, November 27 through Sunday, December 1, 2025, each selected with you in mind.
1. Thanksgiving Dining at Boston’s Top Tables
Date: Thanksgiving Day, Thursday, 27 November 2025
Boston’s culinary scene comes alive this day. Many premier restaurants will offer refined Thanksgiving menus featuring local heirloom turkey, lobster-stuffed roulade, seasonal side dishes, and sumptuous desserts. Consult our Boston restaurant list for inspiration.
2. Boston Celtics at TD Garden
Date: Wednesday, 26 November 2025 — Boston Celtics vs Detroit Pistons at 7:00 p.m. (as noted for Thanksgiving weekend).
3. Black Friday Shopping & Holiday Lights
Date: Friday, 28 November 2025
Back Bay’s luxury boulevards, the newly-lit holiday façade of the shops, and early evening trunk shows set the tone. We are well positioned for you to start your holiday shopping whether that brings you to Newbury Street, Copley Place, The Prudential Center and Seaport.
4. Boston Ballet – “The Nutcracker” Premiere
Date: Friday, 28 November 2025 (season opening) through December 28.
There is something timeless, sophisticated, and seasonally opulent about The Nutcracker. Take in the magic of the Boston Opera House, for one of our favorite Christmas traditions.
5. Faneuil Hall & Quincy Market Tree Lighting Ceremony
Date: Saturday, 22 November 2025 (early kickoff to holiday lighting) — 5:30–6:30 p.m.
A magical moment of city festivity, giving guests a chance to enjoy holiday spirit in an elevated setting without sacrificing comfort. Arrive around 5:00 p.m., then walk through Faneuil Hall to a nearby cocktail lounge afterward. Dress warmly. Discover more about Fanueuil & Quincy Market here.
6. Boston Public Market: Thanksgiving Artisan Shopping
Date: Friday, 21 November through Sunday, 23 November 2025 — Artisan vendors, food offerings, perfect for pre-holiday shopping. If you appreciate craftsmanship and local luxury goods, this offers a refined alternative to mass-market shopping. Visit mid-morning when the vendors open; pick up locally-roasted coffee or a boutique gift before your weekend stay. Boston Public Market Thanksgiving Market
7. Boston Tuba Christmas Concert
Date: Saturday, 30 November 2025 — Downtown Crossing, evening performance of holiday music by over 100 tuba players. This is a unique event probably wasn’t on your holiday calendar bingo card, but this charming cultural moment could the one thing you did this year that no one else has.
8. Winter Waterfront Walk & Early Holiday Market Debut in the Seaport
Date: Sunday, 30 November 2025 — early hours of the holiday-market season by the waterfront While the full market may open in early December, the Seaport district’s early light-ups, pop-up dining huts and waterfront ambiance are available. Read more about Snowport 2025 here.
Your stay at Clarendon Square Inn during Thanksgiving week positions you perfectly to enjoy this refined selection of events—each offering atmosphere, culture, and elegance. Whether you linger over a holiday dinner, take in a performance or simply enjoy a some drinks l in a cozy lounge, Boston offers luxury and warmth in equal measure.