Nantucket Nightlife

The Bar Scene

Nantucket's drinking establishments range from legendary dive bars to sophisticated cocktail lounges. Here's where to head when the sun goes down.

The Chicken Box

14 Dave Street

No conversation about Nantucket nightlife is complete without mentioning "The Box." This legendary dive bar has been the heart of the island's late-night scene for decades. With live music Thursday through Saturday, a packed dance floor, cold cheap beer, and absolutely zero pretense, The Chicken Box is where everyone ends up eventually. Billionaires dance next to bartenders, celebrities rub elbows with fishermen, and everyone has a blast. The music ranges from rock and country to reggae and cover bands, and the energy is infectious. Arrive before 10 PM to avoid the line on summer weekends.

Cisco Brewers

5 Bartlett Farm Road

While technically more of a daytime destination, Cisco Brewers extends well into the evening during summer months. This sprawling campus featuring craft beer, Triple Eight Distillery spirits, and Nantucket Vineyard wines is the perfect transition from beach day to night out. Live music fills the outdoor amphitheater on weekends, food trucks serve up casual eats, and the laid-back vibe makes it easy to lose track of time. It's where many summer nights begin before heading into town.

The Club Car

1 Main Street

For a more sophisticated evening, The Club Car's legendary piano bar is the answer. Housed in an actual 1800s railroad car, this intimate venue features talented pianists playing American songbook classics nightly during summer. Order a perfectly mixed martini, settle into the vintage ambiance, and enjoy the kind of timeless nightlife experience that's increasingly rare. The cocktails are classic, the atmosphere is romantic, and the sing-alongs are encouraged.

Straight Wharf

Straight Wharf area

The bars and restaurants along Straight Wharf offer stunning harbor views as the backdrop for evening drinks. Whether you're at Cru, the raw bar at Straight Wharf Restaurant, or grabbing drinks at one of the waterfront spots, watching the boats bob in the harbor as the stars come out is quintessential Nantucket. The scene is more upscale and tends to quiet down earlier than the downtown bars.

Brotherhood of Thieves

23 Broad Street

Step into Nantucket's maritime past at this atmospheric tavern. With low ceilings, wooden beams, candlelit tables, and the feeling of a genuine whaling-era pub, the Brotherhood is perfect for a cozy pint and good conversation. Their famous curly fries pair perfectly with local craft beers, and the intimate downstairs space fills with a mix of locals and visitors seeking authentic island charm. Not a late-night dance spot, but ideal for an evening of proper pub atmosphere.

Rose & Crown

23 South Water Street

This English-style pub delivers exactly what you'd expect: dark wood interiors, an extensive beer selection, proper pub grub, and a convivial atmosphere where conversations with strangers are part of the experience. The rooftop deck is a summer favorite, and occasional live music adds to the appeal. You'll find locals watching the game, visitors comparing beach notes, and a welcoming vibe that makes everyone feel at home.

Ventuno

21 Federal Street

For a more sophisticated late-night option, Ventuno offers Italian-inspired elegance and stays open later than most. The bar scene is refined but not stuffy, with excellent wines, craft cocktails, and aperitivo options. It's where the stylish set gravitates after dinner, making it a good choice when you want something more upscale than a dive bar but aren't ready to call it a night.

Late-Night Dining Options

When hunger strikes after the bars start closing, options are limited but do exist. Nantucket isn't known for 24-hour diners, but you won't go hungry if you plan ahead.

• The Chicken Box: Basic bar food available during shows
• Pi Pizzeria: Late-night slices when the bars let out (seasonal hours)
• Stubbys: Quick bites downtown open later than most
• Brotherhood of Thieves: Kitchen stays open reasonably late
• Rose & Crown: Pub food until kitchen close
• Ventuno: Late-night menu available at the bar

Pro tip: Eat dinner before going out, as late-night food options are genuinely limited. Most restaurant kitchens close by 10 PM even in high season.

What to Expect

Nantucket nightlife is defined by its casual, friendly atmosphere. Here's what you should know before heading out:

The Vibe

Expect a welcoming, unpretentious scene where everyone's on vacation mode. Conversations start easily, people are generally in good spirits, and the island's small-town charm extends to its nightlife. There's no velvet rope, no bottle service, and no attitude. Even the fancier spots maintain a relaxed New England sensibility.

Dress Code

Essentially, there isn't one. "Nantucket casual" is the universal standard, which means anything from sundresses and sandals to shorts and flip-flops. Even the more upscale spots like Club Car and Ventuno won't turn you away for wearing nice jeans and a collared shirt. The Chicken Box? Anything goes - you'll see people in everything from beach cover-ups to Red Sox jerseys. Pack light and don't stress about dressing up.

The Crowd

Nantucket attracts a diverse mix: families on vacation, young professionals, college kids (especially in summer), longtime summer residents, and locals who've called the island home for generations. The nightlife crowd skews younger at places like The Chicken Box and slightly older at venues like Club Car and Ventuno. One of the island's charms is how all these groups intermingle.

Transportation at Night

Getting around after dark requires some planning. The island's compact size helps, but you'll still need to think ahead.

• Walking: Downtown bars are all within easy walking distance of each other. If you're staying in town, you can easily walk to most venues.
• Taxis: Traditional taxis exist but can be scarce late at night, especially on busy summer weekends. Get phone numbers for local cab companies and call ahead.
• Uber/Lyft: Service is extremely limited on Nantucket. Don't count on ride-sharing apps, especially after midnight. They exist but drivers are few.
• Bikes: Many locals bike everywhere, including to bars. If you do bike, use lights and be extra cautious after drinking.
• Designated Drivers: If your group has a car, designate a sober driver. The island takes DUI seriously.

The best strategy: Stay within walking distance of where you plan to go out, or arrange transportation in advance. Don't count on hailing a cab or finding an Uber at 1 AM.

Safety and Getting Home

Nantucket is generally very safe, but common sense applies:

• Walk with friends: Especially late at night, use the buddy system
• Plan your ride home: Arrange transportation before you go out
• Know your limits: The island's bars will cut you off if needed
• Stay hydrated: Island humidity plus alcohol means drink water
• Keep your phone charged: You'll need it to call a cab
• Watch for bikes: Cyclists are everywhere, even at night

The island has a small but capable police force, and the community looks out for each other. If you find yourself stuck, most bartenders and locals will help you figure out how to get home safely.

Summer vs. Off-Season Nightlife

Peak Summer (June - August)

This is when Nantucket's nightlife truly comes alive. Every venue is open, live music is plentiful, and the energy is high. Expect crowds, especially on weekends. The Chicken Box can have lines out the door by 10 PM, Cisco Brewers is packed all afternoon, and you'll want reservations for dinner anywhere you go. The trade-off for the crowds is an electric atmosphere and endless options.

Shoulder Season (May, September - October)

Many consider this the sweet spot. Most bars and restaurants are still open, but crowds are manageable. You can often walk right into The Chicken Box, find seats at the Club Car piano bar, and enjoy a more relaxed vibe. Fall weekends can still get busy, especially during events like Cranberry Festival.

Off-Season (November - April)

The nightlife scene contracts significantly. Many venues close entirely or operate on extremely limited schedules. The Brotherhood, Rose & Crown, and a handful of local spots remain open and become gathering places for year-round residents. It's a completely different experience - quieter, more local, and with genuine small-town charm. If you visit in winter, embrace the low-key vibe.

Events and Themed Nights

Throughout the season, various venues host special events that are worth planning around:

• Trivia Nights: Several bars host weekly trivia, usually on slower weeknights
• Live Music Schedule: The Chicken Box books bands Thursday-Saturday; check their calendar for lineups
• Cisco Brewery Events: Special beer releases, food truck rallies, and larger concerts
• Holiday Weekends: July 4th, Labor Day, and Memorial Day bring special parties and extended hours
• Wine Tastings: Several venues offer weekly wine events
• Stroll Weekend: Christmas Stroll brings special holiday events to every bar in town

Check local publications like Yesterday's Island, N Magazine, or venue social media accounts for current schedules.

Where Locals Go vs. Tourists

Like any destination, there's some separation between tourist haunts and local favorites:

Local Favorites

• The Chicken Box: Surprisingly, this is where everyone goes - locals and tourists alike
• Rose & Crown: Strong local following, especially during off-season
• Brotherhood of Thieves: Year-round spot for residents
• Downstairs at the Brotherhood: The locals' living room

More Tourist-Heavy

• Straight Wharf area: Beautiful but obviously visitor-oriented
• Club Car: Iconic but well-known to tourists
• Cisco Brewers: Popular with everyone but especially visitors

The truth is, Nantucket's small size means everyone ends up everywhere eventually. There's less separation than you'd find in larger destinations, and locals are generally friendly and welcoming to visitors who respect the island's laid-back culture.

Best Cocktail Bars

For craft cocktails and sophisticated drinks, these venues stand out:

• The Club Car: Classic cocktails in an iconic setting - their martinis are legendary
• Boarding House: Creative, seasonal cocktails with premium ingredients
• Ventuno: Italian-inspired aperitifs and well-crafted classics
• Proprietors Bar & Table: Small-batch spirits and house-made infusions
• Galley Beach: Elegant cocktails with oceanfront sunset views
• Cru: Champagne and wine focus with excellent cocktails at the bar

Expect to pay $14-20 for craft cocktails at these establishments. The quality is worth it.