The end of the world, the start of the party
The Surf Lodge for the day-drinking crowd, Gosman's for the dock seafood, a charter for striped bass off Block Island Sound, sunset cocktails at the Crow's Nest. The Hamptons-adjacent bachelor — beach-coded, fish-coded, expensive in July, perfect in September.
beach • 4-6 hours
Montauk's famous surf beach -- rent boards or just lay out
hiking • 2 hours
Hike to the easternmost point in New York State
fishing • 4-6 hours
World-class sport fishing for striped bass, tuna, and shark
sunset cruise • 2 hours
BYOB catamaran cruise with sunset views of the Montauk coast
bar • unhinged • $$
Montauk's most legendary outdoor party bar with DJs and dancing
lounge • balanced • $$$$
Celebrity-magnet waterfront lounge with live music and sunset views
Dress code: Beach chic
bar • balanced • $$$
Boutique hotel bar with outdoor dance floor and retro summer camp vibes
dive bar • chill • $
Rolling Stones-famous roadside bar with pool table and live music
beer garden • chill • $$
Local craft brewery with outdoor patio and food trucks
pool party • unhinged • $$$$
Resort pool and beach club with DJs, cabanas, and ocean views
Dress code: Resort wear
bar • balanced • $$
Live music venue with local bands and a laid-back surf vibe
bar • balanced • $$
Classic Montauk hangout since 1943 -- fishermen and surfers drink here
cocktail bar • chill • $$$
Craft distillery tasting room with house rum cocktails and ocean-town charm
sports bar • balanced • $$
Casual surf-town sports bar with screens, cold beer, and a backyard patio
Seafood • $$$ • Best for: group-dinner
Waterfront lobster deck on Fort Pond Bay with rosé and sunset views
Seafood • $$ • Best for: dinner
Casual harborfront fish shack with fresh catch and great cocktails
Seafood • $$$ • Best for: group-dinner
Upscale seafood at Gurney's with panoramic ocean views
Bakery • $ • Best for: brunch
Morning pastries and coffee before a beach day
Seafood • $$$ • Best for: group-dinner
Feet-in-the-sand dining with grilled fish and frozen drinks
Seafood • $$ • Best for: dinner
No-frills lakeside fish shack with the freshest lobster rolls
American • $$ • Best for: brunch
All-day cafe popular for brunch smoothie bowls and avocado toast
Pizza • $ • Best for: late-night
Late-night slices and whole pies -- a Montauk tradition since 1957
resort • Max 2 guests
Oceanfront resort with private beach, pool, and spa
boutique-hotel • Max 2 guests
Retro summer camp-style hotel with on-site nightlife
airbnb • Max 12 guests
Full beach houses walking distance to bars and beaches
boutique-hotel • Max 2 guests
Minimalist luxury boutique with private beach and fire pits
The city that never sleeps won't let your party sleep either
Golf clubs, fishing charters, and Montauk dive-bar nightcaps
Track days and five-floor Caroline Street nights
Lake house, wakeboard charter, mountain views
Vineyard crawls, lake fishing, and bourbon barrel tastings with the crew
Cabin weekends, whiskey distilleries, and river fishing
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