Things To Do in Boston This Weekend: February 20 – February 22
Boston’s late-winter calendar delivers big flavors, big laughs, and inventive live experiences. From Dine Out Boston turning the city into a prix fixe playground to Jo Koy: Just Being Koy Tour…

LAS VEGAS, NEVADA – APRIL 27: Jo Koy speaks onstage during CinemaCon 2022 – Universal Pictures and Focus Features Invites You to a Special Presentation Featuring Footage from its Upcoming Slate at The Colosseum at Caesars Palace during CinemaCon, the official convention of the National Association of Theatre Owners, on April 27, 2022 in Las Vegas, Nevada. (Photo by Frazer Harrison/Getty Images for for CinemaCon)
Boston's late-winter calendar delivers big flavors, big laughs, and inventive live experiences. From Dine Out Boston turning the city into a prix fixe playground to Jo Koy: Just Being Koy Tour and the genre-blending magic of Candlelight: 90s Hip-Hop on Strings, this lineup balances indulgence, humor, and creativity with high-energy concerts to keep the momentum going.
Dine Out Boston
- What: Dine Out Boston (Formerly Restaurant Week Boston)
- When: Sunday, Feb. 22 through Saturday, Mar. 7, 2026
- Where: Over 143 restaurants in Boston, Massachusetts
- Cost: Varies by menu items and restaurant; lunch options range from $27 to $36, and dinner options range from $38 to $55.
Dine Out Boston returns this year with more than 175 participating restaurants, offering special pricing on their menus. For three weeks, Boston's food scene features wonderfully put-together meals at a wide range of price points. Visit Atlantic Fish Co. for some of the freshest seafood you will ever have, Mamma Maria for authentic Italian food, or Grill 23 & Bar for a high-end steakhouse experience. Presented by Meet Boston, this biannual celebration offers a delicious way to sample the city's best flavors in one unforgettable season.
Jo Koy: Just Being Koy Tour
- What: Comedian Jo Koy
- When: Friday, Feb. 20, and Saturday, Feb. 21, 2026, at 8 p.m.
- Where: Boch Center, Wang Theatre, 270 Tremont St., Boston
- Cost: Tickets start at $34.50
Jo Koy is a comedy force right now, having gone from nothing to being one of the biggest names in comedy on the planet. In addition to winning “Standup Comedian of the Year,” he has released numerous successful comedy albums, produced several specials on Netflix and Comedy Central, and established himself as one of the top ten performers over the past twenty-five years. By seamlessly combining personal stories with cultural humor and with his ability to create relatable comedy, he is creating a legacy that will last for generations.
Candlelight: 90s Hip-Hop on Strings
- What: 90s hip-hop, reimagined by strings
- When: Friday, Feb. 20, 2026, at 9 p.m.
- Where: Simons Theatre, New England Aquarium, 1 Central Wharf, Boston
- Cost: Tickets start at $52.50
Fever's Candlelight: 90s Hip-Hop on Strings reimagines classic '90s rap and hip-hop through elegant, string-quartet arrangements. Candlelight creates an iconic atmosphere, where songs by Jay-Z, OutKast, Wu-Tang Clan, and 2Pac are reimagined as chamber music. This process bridges different types of music and eras. It's a unique concert experience blending nostalgia, live performance, and an evocative atmosphere for fans of both hip-hop and instrumental music.
Other Events
From cage-fighting intensity and family-friendly magic to a pulse-pounding rock show, Boston brings bold entertainment and big reactions to the spotlight.
- Cage Titans: Revolution. Saturday, Feb. 21, 2026, at 5:30 p.m. at MGM Music Hall at Fenway, 2 Lansdowne St., Boston
- Mario the Maker Magician. Friday, Feb. 20, 2026, at 3 p.m. and 6 p.m.; Saturday, Feb. 21, 2026, at 2 p.m. and 5 p.m.; and Sunday, Feb. 22, 2026, at 1 p.m. and 4 p.m. (additional dates/times available through Sunday, Mar. 1, 2026) at The Roberts Studio Theatre, 527 Tremont St., Boston
- Nothing More With Catch Your Breath, Archers, and Doobie. Friday, Feb. 20, 2026, at 5:30 p.m. at Music Hall, Citizens House of Blues Boston, 15 Lansdowne St., Boston
More To Explore This Week
Weeknights get a serious glow-up with shows that turn ordinary evenings into standout moments. These picks bring just the right spark to break the weekday routine and keep the energy buzzing all week long.
- Eleni Drake. Monday, Feb. 23, 2026, at 7:30 p.m. at Haymarket Lounge at City Winery Boston, 80 Beverly St., Boston
- Darcy & Jer: Average At Best Tour. Tuesday, Feb. 24, 2026, at 8 p.m. at Boch Center, Shubert Theatre, 270 Tremont St., Boston
- Conan Gray. Wednesday, Feb. 25, 2026, at 8 p.m. at TD Garden, 100 Legends Way, Boston
- 31st Annual Write of Spring Concert. Thursday, Feb. 26, 2026, at 7:30 p.m. at David Friend Recital Hall (DFRH), 921 Boylston St., Boston




