Start late-morning in Central Square with a browse through the racks at Cambridge Antique Market, where you and your niece can hunt for quirky vintage accessories, weird little décor pieces, and one-of-a-kind finds that feel perfectly Cambridge. Then head to Harvard Square for a stop at The Garage, where you can mix thrift shopping with an indie-book detour at Harvard Book Store and a casual lunch nearby, keeping the vibe easy, funky, and fun before the live-music portion of the day.
Spend the afternoon in Inman Square, where the mood shifts nicely into a more local, offbeat Cambridge rhythm with a stop at The Garment District for a deep dive into racks of vintage clothing, costume-y treasures, and playful pieces your niece can try on just for fun. After that, ease into a relaxed lunch at S&S Restaurant or a similarly casual neighborhood spot, then wander toward The Middle East for an early evening set or live-music check-in if the timing lines up, giving you that playful, slightly unexpected finish that keeps the day feeling distinctive and teen-friendly.
As evening settles in, head to Davis Square for a fun final stretch at Redbones or another easygoing spot for barbecue, fries, or a casual early dinner that feels laid-back after a day of wandering. Then make your way to Club Passim in Harvard Square for live music in an intimate, iconic room that keeps the night feeling distinctly Cambridge, with a cozy, teen-friendly vibe and a great chance to end the day with something memorable and a little different.