❤️ Hey South Shore,

Valentine’s Weekend has arrived, and the plans this time around feel a little more open-ended. Some nights lean toward big shows and packed rooms, others stay quieter and more intentional. There’s no single way this weekend is supposed to look, and that’s part of the appeal.

This guide brings together Broadway laughs, live music, late-night energy, and a few daytime options that keep things flexible. Whether you’re planning something specific or deciding as you go, here’s what’s happening across the South Shore from Feb 12 through Feb 15.

Bright costumes, rapid-fire jokes, and a cast that never lets the momentum dip. Spamalot leans fully into Monty Python’s absurdity, stacking sight gags, clever wordplay, and familiar musical numbers into a show that moves fast and stays playful. The CM Performing Arts Center’s intimate stage keeps the comedy close and the laughs constant rather than sprawling. This is a strong pick if you want Valentine’s Weekend plans that favor humor over sentiment.

When: Opens Sat, Feb 14 | Runs through Mar 1
Where: CM Performing Arts Center, Oakdale
Price: $$+
😂 See showtimes

Big vocals, disco-era glamour, and a room that leans into the joy of it all. Rainere Martin brings Donna Summer’s catalog to life with power and polish, moving easily from dance-floor anthems to soulful ballads. The pacing stays energetic without feeling rushed, and the Boulton Center’s seated setting keeps the night comfortable and celebratory rather than chaotic. This works especially well for Valentine’s Weekend if you want something upbeat that still feels classic.

When: Fri, Feb 13 | 8 PM
Where: Boulton Center for the Performing Arts, Bay Shore
Price: $$+
💃 Book your seats

This one is built for momentum. O El Amor sets the tone with lively Latin-pop energy, then Vinyl Revival keeps the floor moving with familiar crowd-pleasers. The room fills quickly, the drinks flow easily, and the vibe stays social from start to finish. A strong pick for couples or groups who want to start Valentine’s Weekend with dancing rather than sitting still.

When: Fri, Feb 13 | 7–11 PM
Where: 89 North Music Venue, Patchogue
Price: $$
🕺 Grab tickets

Dinner, drinks, and a storyline that pulls the room together. Fire Island Vines turns Valentine’s night into something playful with an interactive murder mystery where guests become part of the story. The pacing stays light, the crowd stays engaged, and the experience feels more fun than formal. A solid option if you want Valentine’s plans that spark conversation and don’t take themselves too seriously.

When: Sat, Feb 14 | 6–10 PM
Where: Fire Island Vines, Bay Shore
Price: $$+
🕵️ Reserve your spot

A night rooted in guitar-driven blues and unmistakable stage presence. Billy F Gibbons brings his signature Texas sound to Patchogue with a tight trio setup that keeps the focus squarely on musicianship. The theatre setting adds clarity and comfort, letting the music carry the evening without distraction. This is a confident, no-frills pick for classic rock fans who want a show that delivers exactly what it promises.

When: Sat, Feb 14 | 8 PM
Where: Patchogue Theatre for the Performing Arts, Patchogue
Price: $$+
🎸 Get tickets

A calm, creative afternoon built around music kids already love. This Taylor Swift–themed painting workshop gives school-age children space to create while listening to familiar songs, keeping the energy focused without feeling rigid. The library setting keeps it structured and relaxed, making it a good fit for kids who enjoy art with a little inspiration woven in. This works best for families looking for something hands-on that still feels low-key and organized.

When: Thu, Feb 12
Where: Sayville Library, Children’s Activities Room
Price: Free (registration required)
🎨 Reserve a spot

A festive Valentine’s morning designed with little kids in mind. Open play, snacks, and a meet-and-greet with Mickey and Minnie keep things moving while still leaving room for parents to relax. Each child decorates a Valentine’s cookie to take home, adding a simple keepsake to the experience. This is a good option if you want something cheerful and contained without committing the whole day.

When: Sat, Feb 14 | 10:30 AM–12 PM & 1:30 PM-3 PM
Where: La La Land, Babylon
Price: $$
❤️ Book your session

A slightly longer Valentine’s celebration with room to roam. My Play Space leans into open play, themed crafts, music, and photo moments, creating a flexible flow that works well for young kids. The setting stays lively without being overwhelming, and the pace allows families to move through activities naturally. This is a solid pick if your child does best with options rather than a fixed schedule.

When: Sat, Feb 14 | 11:30 AM–1 PM
Where: My Play Space, Babylon
Price: $$
🎈 Save your spot

A classic Valentine’s setup done the traditional way. Lombardi’s pairs a full dinner, open bar, and DJ-led dancing in a waterfront space that already feels like an occasion. The night moves at an easy pace, giving couples time to eat, talk, and eventually make their way to the dance floor without feeling rushed. This works best if you want a polished evening that handles everything in one place.

When: Fri, Feb 13 | 7–11 PM
Where: Lombardi’s On The Bay, Patchogue
Price: $$+
💃 Reserve your table

Smooth harmonies, familiar lyrics, and a seated theater that keeps the night comfortable. Fast Lane recreates The Eagles’ catalog with precision, delivering a polished tribute that feels nostalgic without feeling dated. The Boulton Center’s intimate setting makes it easy to settle in and enjoy the music together. A strong pick for couples who prefer listening over loud crowds.

When: Sat, Feb 14
Where: Boulton Center for the Performing Arts, Bay Shore
Price: $$+
🎸 Book your seats

A creative Valentine’s plan that stays relaxed and approachable. This guided paint-and-sip draws inspiration from Keith Haring’s heart imagery, making it playful without requiring art experience. The format leaves room for conversation while still giving the night a shared focus. Ideal if you want something interactive that still feels calm and low-pressure.

When: Sat, Feb 14 | 5–7 PM
Where: Islip Arts Council, Islip
Price: $$
🎨 Save your spot

Valentine’s night for people who would rather hear guitars than love songs. Three tribute acts bring heavy riffs and high-energy sets inspired by Alice In Chains, Green Day, and Red Hot Chili Peppers. The room stays loud, the crowd stays moving, and the vibe leans more release than romance. Best for couples who bond over live music and volume.

When: Sat, Feb 14 | 7–11 PM
Where: 89 North Music Venue, Patchogue
Price: $$
🤘 Grab tickets now

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