While New Canaan is known for its charming downtown by day, it also offers a **surprisingly lively nightlife scene**—from cozy wine bars to live music hotspots. Whether you're looking for craft cocktails, trivia nights, or late-night bites, here’s your guide to evening fun.

Best Bars & Lounges

1. The Roger Sherman Inn Pub

A **classic Connecticut tavern** with craft beers, whiskey flights, and live piano on weekends.

Vibe: Upscale rustic

Tip: Try their signature "Sherman Manhattan."

2. South End

Sophisticated **craft cocktail bar** with an impressive Italian wine list and late-night pizza.

Must-order: The "Bergamot Fizz" (gin, citrus, prosecco)

Live Music & Events

3. The Glass House Jazz Series

Seasonal **jazz nights** at Philip Johnson's iconic Glass House (BYO picnic).

When: Select summer evenings

4. New Canaan Brewing Company

Local microbrewery with **trivia nights** and rotating food trucks.

Try: "Elm Street IPA" (their flagship brew)

Late-Night Eats

🍔 Gates Restaurant

Open until **11 PM** (Fri/Sat) for post-bar cravings.

🍕 Solé

Late-night slices until **midnight** on weekends.

Seasonal Nightlife Events

Don't miss these annual highlights:

• Summer Stroll: Evenings with extended patio hours and live music
• Oktoberfest: Beer garden pop-up at New Canaan Brewing Co
• New Year's Eve: Champagne toasts at downtown bars

Local Nightlife Tip

Many bars offer **weekday specials**—like half-price wine bottles on Wednesdays at South End.

Parking & Transportation

Most bars are within walking distance downtown. Pro tips:

• Parking: Free after 6 PM in all town lots
• Rideshares: Easy Uber/Lyft access to nearby towns
• Metro-North: Last train to NYC departs ~1 AM