18 Things to Do in Boston This Week · May 21–24, 2026

Festivals & Special Events

The Big Gig: Spring Music Festival & Market

A spring music festival and market at the Charles River Speedway running over the Memorial Day weekend.

Saturday, May 23, 2026 · The Charles River Speedway

4th Annual Asian Street Food & Music Festival

Free, family-friendly festival featuring authentic Asian street food, live performances, a beer garden, karaoke, games, vendors, and a Cosplay contest in Cambridge.

Sunday, May 24, 2026 · Cambridge

The WBUR Festival

Two days of lively conversations, podcast tapings, and musical performances at Boston University.

Friday, May 29, 2026 · Boston University

Greenway Food Truck and Fitness Festival

A free festival combining food trucks and outdoor fitness activities along Boston's Greenway at Rowes Wharf Plaza.

Saturday, May 30, 2026 11:00 AM · Rowes Wharf Plaza, Boston

The Curl Bar Block Party 4.0

The Curl Bar's fourth annual block party returns with community, music, and celebration in the North End.

Saturday, May 30, 2026 12:00 PM · 92 Cross St, Boston

Free Events

Memorial Day Flag Garden – Boston Common

Thousands of flags planted on Boston Common in honor of Massachusetts service members who gave their lives — a quietly powerful tribute worth sharing with kids.

Thursday, May 21, 2026 · Boston Common, Boston

Lilit Hartunian at Museum of Fine Arts

Live music performance by Lilit Hartunian at the MFA Boston as part of the Sound Bites Nancy Lee Clark Concert Series.

Thursday, May 21, 2026 6:00 PM · Museum of Fine Arts, Fenway, Boston

Free MFA Admission on Memorial Day 2026: Museum of Fine Arts Open House

The Museum of Fine Arts opens its doors for free to all visitors on Memorial Day.

Monday, May 25, 2026 10:00 AM · Museum of Fine Arts, Boston

Music & Nightlife

Colin Quinn at The Wilbur

Stand-up comedy legend Colin Quinn takes the stage at The Wilbur for one night only.

Friday, May 22, 2026 7:30 PM · The Wilbur, Boston

Comedy Night w/ Boston's Best @ Elephant & Castle

A stand-up comedy showcase featuring Boston's best comedians at the downtown Elephant & Castle pub.

Saturday, May 23, 2026 8:00 PM · Elephant & Castle, Downtown Boston

GBH Jazz Night with Tiger Okoshi: A Tribute to Miles Davis

Jazz fusion trumpeter Tiger Okoshi performs a Miles Davis tribute concert in honor of Davis's 100th birthday, presented by GBH Music and JazzBoston at the Boston Public Library.

Thursday, May 28, 2026 5:30 PM · Boston Public Library, Boston

Summer Kickoff Party – BostonYPA

Boston's Young Professionals celebrate summer with an outdoor party at Club Volo at Assembly Row.

Friday, May 29, 2026 6:00 PM · Club Volo @ Assembly Row, 300 Grand Union Blvd, Somerville

Arts & Culture

The Nature Plays at Mount Auburn Cemetery

Short theatrical fragments staged right in the cemetery, created by playwright-in-residence Patrick Gabridge, drawing from research into the cemetery's biodiversity.

Saturday, May 23, 2026 · Mount Auburn Cemetery, 580 Mount Auburn St., Cambridge

LGBTQ+ Coro Allegro: Luminous Rescue – Psalms of Protest and Reconciliation

Boston's LGBTQ+ choral ensemble Coro Allegro performs a powerful program of psalms of protest and reconciliation at Church of the Covenant.

Sunday, May 24, 2026 3:00 PM · Church of the Covenant, Boston

HellaBlack Vol. 8: Genesis

The HellaBlack exhibition series returns for its 8th volume at the Boston Center for the Arts in the South End, opening May 29.

Friday, May 29, 2026 · Boston Center for the Arts, South End

Outdoors & Active

SoWa Open Market

Artisans, craftspeople, designers, and local farmers gather in Boston's South End art district every Sunday from May through November.

Sunday, May 24, 2026 11:00 AM · SoWa Boston, 530 Harrison Ave, South End

Date Night

Marc E. Bassy at City Winery Boston

R&B singer-songwriter Marc E. Bassy performs an intimate concert at City Winery Boston, pairing live music with dinner service and award-winning wines.

Friday, May 29, 2026 7:30 PM · City Winery Boston, 80 Beverly Street

Food & Drink

Museum of Ice Cream x New City Microcreamery Launch Party

A launch party collaboration between the Museum of Ice Cream and New City Microcreamery, blending immersive art and artisanal ice cream.

Wednesday, May 27, 2026 7:00 PM · Museum of Ice Cream, Boston