The Boston Almanac

Curated weekly · Est. 2026

Date Night Ideas

2026-05-26 2026-06-04 · 150 entries

01

Two'sDay Night Dinner Date

95/100

Prix fixe dinner for two at a wine bar is an intimate and romantic date-night experience.

  • 3:00 pm–9:00 pm
02

Jacob Collier

95/100

Jacob Collier's genre-bending performance at Symphony Hall is a spectacular date-night concert.

  • 7:30 pm–9:30 pm
03

Boston Ballet: The Sleeping Beauty

95/100

Boston Ballet's The Sleeping Beauty is a world-class, romantic date-night performance.

  • 7:30 pm–3:30 pm
04

Jacob Collier

95/100

Jacob Collier at Symphony Hall is a world-class musical date-night experience.

  • 7:30 pm–9:30 pm
05

Coolidge @ The Speedway 2026

90/100

Free outdoor movie series curated by Coolidge, perfect romantic summer date.

  • 7:30 pm–11:00 pm
07

Harvard Art Museums at Night

90/100

An evening at the Harvard Art Museums with art, food, and drinks is a sophisticated date.

  • 5:00 pm–9:00 pm
08

Jazz Fridays at The Fed

90/100

Jazz Fridays at a stylish hotel bar offer an intimate, sophisticated date-night atmosphere.

  • 6:00 pm–9:00 pm
11

PAGU: Sushi & Hand-Roll Class

90/100

A sushi-making class is an interactive and delicious date activity.

  • 1:00 pm–3:00 pm
13

Whole Note Wednesdays at The Liberty Hotel

90/100

Acoustic jazz in the Liberty Hotel lobby is a sophisticated and romantic date-night setting.

  • 6:30 pm–9:30 pm
14

Ben Folds

90/100

Ben Folds at Symphony Hall is a world-class concert experience for a memorable date night.

  • 7:30 pm–9:30 pm
16

Central Square Food and Mural Arts Tour

85/100

Food and mural arts tour is a perfect date-night activity combining culture and cuisine.

  • 7:00 pm–9:00 pm
17

Live Music Tuesdays at Telegraph Hill

85/100

Live music at a bar is a classic and romantic date-night activity.

  • 7:30 pm–10:00 pm
19

Black Swan: A New Dance Thriller

85/100

Black Swan dance thriller at A.R.T., excellent for a date night.

  • 12:00 pm
22

McCarthys Cambridge Irish Session

85/100

Live Irish music session at a pub, lively and romantic date night.

  • 7:00 pm–10:00 pm
24

Revolutionary Spirits: Libations for Preservation

85/100

A networking cocktail hour at a historic cocktail club celebrating preservation is a sophisticated date-night event.

  • 7:00 pm–10:00 pm
27

Free Thursdays at the ICA

85/100

Free Thursday nights at the ICA offer a cultured and budget-friendly date.

  • 5:00 pm–9:00 pm
29

Clear Voices in the Dark

85/100

A choral performance at a beautiful venue is a sophisticated date-night choice.

  • 7:00 pm–8:30 pm
30

Skylark

85/100

A Grammy-nominated choral performance is a sophisticated date-night choice.

  • 7:00 pm–8:30 pm
31

A Jazz Evening with Jacques Schwarz-Bart

85/100

Jazz trio performance at an intimate venue is a perfect date-night event.

  • 6:00 pm–7:30 pm
34

Zaccai Curtis

85/100

Grammy-winning jazz pianist in an intimate hall is a superb date-night concert.

  • 7:30 pm–9:00 pm
35

Live Jazz in Brookline!

85/100

Live jazz with multiple sets in an underground venue is a perfect date-night music experience.

  • 7:30 pm–11:00 pm
36

An Evening with Megan Hilty

85/100

Broadway star in concert at an arts center is a polished, romantic date-night event.

  • 8:00 pm–9:30 pm
37

An Evening with Darren Criss

85/100

Tony-nominated star in a one-night-only concert is a spectacular date-night event.

  • 8:00 pm–10:00 pm
38

Smerz at Institute of Contemporary Art Boston

85/100

Live electronic music at a contemporary art museum makes for a sophisticated and memorable date night.

  • 8:00 pm–11:00 pm
42

The Lemon Drop Social Club

85/100

A hands-on mixology class is an interactive and romantic date.

  • 6:00 pm–9:00 pm
43

Millennial Speed-Dating (Monogamous)

85/100

Millennial speed dating is directly aimed at singles seeking dates.

  • 7:00 pm–9:00 pm
46

Full Moon Rise over Boston

85/100

Watching the full moon rise from a park is a romantic, scenic date.

  • 7:45 pm–8:45 pm
50

Vivaldi with Symphony by the Sea

85/100

A Vivaldi concert at a museum is a refined date experience.

  • 2:00 pm–4:00 pm
52

The Beach Boys

85/100

Classic Beach Boys concert at an intimate theater, perfect for a nostalgic date night.

  • 8:00 pm–10:00 pm
54

Major Mondays at the Liberty Hotel

85/100

Live blues music in the Liberty Hotel lobby, a sophisticated and romantic date-night setting.

  • 6:30 pm–9:00 pm
55

Two'sDay Night Dinner Date

85/100

Weekly prix fixe dinner for two at a wine bar, perfectly designed for a romantic date night.

  • 3:00 pm–9:00 pm
58

Anjimile

85/100

An intimate concert by a Boston-based singer-songwriter at a small venue is perfect for a date.

  • 7:00 pm–9:00 pm
59

Free Swing Dance and Lesson

85/100

Free swing dance with a lesson at a historic hall is a romantic and lively date-night activity.

  • 8:00 pm–11:00 pm
60

Porto Vino Italian Wine Dinner

85/100

Italian wine dinner at a supper parlor, elegant and romantic for a date.

  • 6:30 pm–8:30 pm
62

Use the Force/Carboy

85/100

Live funk/jazz band at Lizard Lounge, perfect for a lively date night.

  • 8:00 pm–11:00 pm
64

PhotoWalks Freedom Trail tour

80/100

Freedom Trail walking tour is a great daytime date activity.

  • 1:15 pm–2:45 pm
65

PhotoWalks North End Tour

80/100

North End walking tour is a wonderful daytime date exploring history and food.

  • 1:30 pm–2:45 pm
67

25th Anniversary! SHREK • Free!

80/100

Free screening of Shrek is a fun and nostalgic date-night movie event.

  • 6:00 pm–8:00 pm
69

McCarthys Cambridge Irish Session

80/100

Live Irish music session is a lively and authentic date-night experience.

  • 7:00 pm–10:00 pm
71

Candle Making/Intention Setting

80/100

Candle-making workshop is a creative and romantic date-night activity.

  • 7:00 pm–8:30 pm
72

FREE Live Standup - Laugh Giraffe

80/100

Free standup comedy show is a fun and affordable date-night activity.

  • 8:00 pm–9:30 pm
74

Solo Violin baroque lunch concert

80/100

Solo baroque violin concert at King's Chapel, intimate and romantic.

  • 12:15 pm
75

Trivia @ Town Tavern

80/100

Trivia night at a tavern with food and drinks, classic date-night activity.

  • 6:30 pm–8:30 pm
77

PASTA MAKING NIGHT

80/100

Pasta-making class at an Italian restaurant, hands-on and romantic.

  • 5:30 pm–8:30 pm
78

Lydian String Quartet: An Open Rehearsal

80/100

An intimate open rehearsal by an award-winning string quartet is a refined cultural date.

  • 7:30 pm–9:00 pm
79

Free Swing Dance and Lesson

80/100

Free swing dance lesson and social dancing is a fun, active date night.

  • 8:00 pm–11:00 pm
80

Wednesday Evening Walk

80/100

A guided evening walk through Beacon Hill is a romantic and scenic date.

  • 6:00 pm–7:30 pm
84

Live Music at Time Out Market

80/100

Live music at a food hall creates a lively and casual date atmosphere.

  • 6:00 pm–9:00 pm
  • 6:00 pm–9:00 pm
  • 6:00 pm–9:00 pm
85

75th Anniversary! THE LAVENDER HILL MOB

80/100

A classic film screening at the Brattle Theatre is a charming date-night choice.

  • 6:00 pm–7:30 pm
86

Live Music Thursdays in Back Bay

80/100

Live music at a hotel bar creates a sophisticated and romantic date atmosphere.

  • 6:00 pm–9:00 pm
87

McCarthys Cambridge Irish Session

80/100

Live Irish music at a pub is a lively and authentic date-night experience.

  • 7:00 pm–10:00 pm
89

PASTA MAKING NIGHT

80/100

Pasta making class is a hands-on and romantic date-night activity.

  • 5:30 pm–8:30 pm
90

Naomi Watanabe - From Tokyo 2026 Tour

80/100

Headlining comedy tour from a Japanese star is a unique, high-energy date-night show.

  • 6:30 pm–9:30 pm
92

Naomi Watanabe: FROM TOKYO

80/100

Comedy tour from a Japanese star is a unique, high-energy date-night show.

  • 7:30 pm–10:00 pm
93

Eureka Day

80/100

Award-winning satire about progressive parents is a sharp, entertaining date-night play.

  • 7:30 pm–2:00 pm
94

Marc E. Bassy

80/100

Intimate concert by genre-bending artist at a winery is a romantic date-night experience.

  • 7:30 pm–9:00 pm
95

Happy Couples Game Show

80/100

Interactive couples game show at a winery is a playful, romantic date-night event.

  • 7:30 pm–9:00 pm
96

City Cinderella: A Bridgerton Ball

80/100

Bridgerton-themed drag ball is a glamorous, immersive date-night spectacle.

  • 7:30 pm–10:00 pm
97

Date Night: Paint Your Partner

80/100

Paint-your-partner night is a creative, romantic date-night activity.

  • 10:00 am
99

El Último Sueño de Frida y Diego

80/100

Met Opera performance at a beautiful venue is a sophisticated and romantic date.

  • 1:00 pm–3:30 pm
100

Shakespeare's Romeo and Juliet

80/100

Shakespeare's Romeo and Juliet at the Strand Theatre is a classic romantic date.

  • 2:00 pm–3:30 pm
101

How To Train Your Dragon – In Concert

80/100

Film with live symphony orchestra at Symphony Hall is a spectacular date.

  • 7:30 pm–9:30 pm
102

Country Night at West End Johnnie's

80/100

Country night with dancing and drinks offers a fun, energetic date-night experience.

  • 9:00 pm–12:00 am
103

Opening Reception: Wandering the City

80/100

An art opening reception is a sophisticated and romantic date option.

  • 4:00 pm–6:00 pm
105

Connor King in Boston!

80/100

A stand-up comedy show is a fun and classic date-night activity.

  • 8:00 pm–9:30 pm
109

Butterfly Vase; Glass Fusing Class

80/100

A glass fusing class to create a butterfly vase is a creative date.

  • 2:00 pm–5:00 pm
110

Live Music Sundays

80/100

Live music at a brewery taproom is a classic Sunday date.

  • 2:00 pm–5:00 pm
111

Bone & Water Ghost Tour Lowell

80/100

A ghost tour is a spooky and memorable date activity.

  • 2:30 pm–6:00 pm
118

Barbara Pierre - Everyday Smiles

80/100

An intimate night of soulful music is a perfect date.

  • 6:00 pm–7:00 pm
119

Boston Cake Decorating

80/100

A cake decorating class is a sweet and interactive date.

  • 6:00 pm–7:00 pm
121

McCarthys Irish Session

80/100

Live Irish music at a pub is a cozy and lively date.

  • 7:00 pm–10:00 pm
123

Comedy at The 88 Club (Free!)

80/100

Free stand-up comedy in Back Bay is a great date option.

  • 7:30 pm–9:00 pm
125

Partner Swing Dancing at Loretta's

80/100

Partner swing dance lessons every Monday, a fun and romantic date-night activity.

  • 7:00 pm–10:00 pm
126

Ann Wilson - In My Voice

80/100

Ann Wilson documentary screening and Q&A, a special and memorable date-night event.

  • 7:30 pm–9:00 pm
128

2026 Greek Heritage Night at Fenway Park

80/100

Greek Heritage Night at Fenway combines a Red Sox game with cultural celebration for a memorable date.

  • 6:45 pm–10:45 pm
129

Central Square Food and Mural Arts Tour

80/100

Food and mural arts tour offers a delicious and cultural evening date experience.

  • 7:00 pm–9:00 pm
130

Paolo Angeli

80/100

Live performance by Paolo Angeli at City Winery offers an intimate concert and dining date.

  • 7:30 pm–9:00 pm
131

Spanish And Latin Fire - Kasia Smolarek

80/100

Spanish and Latin guitar concert at Old South Church is a beautiful and romantic date.

  • 7:30 pm–8:45 pm
132

Live Music Tuesdays at Telegraph Hill

80/100

Live music every Tuesday at a bar with no cover is a relaxed and enjoyable date.

  • 7:30 pm–10:00 pm
133

FREE Live Standup - Laugh Giraffe

80/100

Free standup comedy showcase is a hilarious and budget-friendly date-night activity.

  • 8:00 pm–9:30 pm
136

Tufting (Make your own rug)

80/100

Making your own rug at a craft studio is a creative and hands-on date experience.

  • 3:30 pm–7:30 pm
137

Beach Reads Book Fair at Sam Adams

80/100

A beach reads book fair at a taproom combines books and beer for a charming date.

  • 5:30 pm–8:30 pm
141

McCarthys Cambridge Irish Session

80/100

Live Irish music sessions at a pub are a lively and romantic date-night experience.

  • 7:00 pm–10:00 pm
142

Stephen Lynch: The Me Tour

80/100

Stephen Lynch's comedic music show at City Winery is a fun and intimate date-night concert.

  • 7:30 pm–9:00 pm
147

Painted Burro Waltham- Happy Hour Deals!

75/100

Happy hour with half-priced appetizers and tacos is a casual and fun date option.

  • 2:00 pm–5:00 pm
148

$1 Oysters at Gray's Hall

75/100

Dollar oysters are a fun and affordable date-night treat.

  • 4:00 pm–10:00 pm
149

Posto South End- Happy Hour Deals!

75/100

Happy hour with half-priced appetizers is a great pre-dinner date stop.

  • 5:00 pm–6:00 pm
150

$1 Oysters at Vera's!

75/100

Dollar oysters are a fun and affordable date-night treat.

  • 5:00 pm–6:00 pm