Exploring Montauk, New York in Two Days
Let's Jet Off to the End: Your Ultimate Weekend Guide to Montauk
Updated 06/16/2025 | Originally published 04/26/2019
FRIDAY
4 pm: Seafood Pit Stop
After cruising past East Hampton, you're almost at the tip of Long Island's South Fork and Montauk. On your way, grab a bite at either The Lobster Roll or Clam Bar at Napeague (open seasonally). Prefer something heartier? Try out a succulent lobster roll, a dozen local oysters, or even an early dinner with a catch straight from the day-boat to kick off your beach holiday right!
5:30 pm: Bed Down for the Night
New Montauk hotels are as classy as the area itself. Whether you opt for a small chic motel like Hero Beach Club or the palatial Gurney's Montauk Resort & Seawater Spa, you'll find yourself just steps away from the beach, parks, and shopping.
9 pm: Dine with Panache at South Edison
Fancy a taste of the refined side of Montauk? Head to South Edison for their fresh seafood menu in a sleek, coastal dining room that seamlessly mixes the city with the beach.
SATURDAY
7 am: Rise and Shine - Time for Some Fishing!
Love fishing? Montauk has a variety of options to cater to your seaside cravings. Book a private charter or try casting a line from the docks on Montauk Harbor with reputable operators like Viking Fleet, Ebb Tide, or Miss Montauk II.
9 am: Breakfast at Montauk Bake Shoppe
Wake up to a delicious spread at Montauk Bake Shoppe, one of the town's best breakfast spots. Grab their famous fried jelly croissant, an egg sandwich on a fresh-baked bagel, or a cruffin—locals swear by it! Don't forget to share the buttermilk pancakes or French toast with the kids. Montauk Bake Shoppe has been serving the town since the 1960s.
10:30 am: Step Back in Time at Montauk Lighthouse
Experience the stunning Montauk Point—home of the 1796 Montauk Lighthouse. This iconic structure dates back to President George Washington and houses a museum that offers insider stories about its rich history. Enjoy the inspiring views, serene bluffs, and picturesque beach—and if you're here between November and April, don't forget to take a stroll along the shore; seals love the rocks!
1 pm: Refuel Your Energy with a Lunchtime Feast at Inlet Seafood Restaurant
Head back to the village and demand a table at Inlet Seafood Restaurant. This oceanfront stunner offers a taste of Montauk's soul with its succulent sushi, delicious lobster rolls, mouthwatering burgers, and even a house-made pesto pasta. If you can't make it for lunch, a sunset dinner here is simply unforgettable.
3 pm: Soak Up the Sun on the Beach
Discover the vibrant sandy shores of Montauk. Ditch the car and spend the rest of your afternoon at Kirk Park Beach. With its lifeguards, restrooms, and a usually appealing surf, this beach is perfect for soaking up the sun, playing in the waves, or building the best sandcastles.
5 pm: Quench Your Thirst at Montauk Brewing Company
Just a short walk from Kirk Park Beach awaits the picturesque tasting room for Montauk Brewing Co. Delight in a flight of local brews celebrating Montauk's spirit, from the crisp pilsner to the award-winning, hoppy IPAs. Sip your favorite while the kids will adore a fun round of mini-golf at Puff 'N' Putt (open seasonally).
6 pm: Choose Your Sunset Vantage Point
Montauk sunsets are legendary. Whether you're in the mood for a romantic cocktail at Navy Beach or a chilled-out vibe with lobster on the docks at Duryea's, the spectacular sunset is a defining part of Montauk. If you're craving a leisurely stroll, meander along the coast at your own pace.
8 pm: Savor Dinner at Gigi's Montauk
Still ravenous? Satisfy your cravings at Gigi's Montauk—the new dining sensation at Gurney's Montauk Resort. Their impressive menu features decadent seafood towers, fresh oysters, locally-sourced fish, succulent steaks, handmade pasta, and irresistible desserts—the perfect ending to a truly Mediterranean dining experience.
SUNDAY
9 am: Surf's Up! (Optional)
Surf's up! Take a surfing lesson with one of Montauk's many expert teachers, like Coreyswave, or explore the waves solo. Make sure to reserve your lesson during busy summer weekends. If sand and surf aren't your cup of tea, try booking a tee-time at Montauk Downs State Park Golf Course, a picturesque 18-hole course with ocean views that dates back to 1927.
12 pm: More Seafood at 668 The Gig Shack
Fancy a bite after all that fun? Check out 668 The Gig Shack, where you can indulge in fresh dishes like scallop and shrimp tacos, classic lobster rolls, delectable burgers, and even a grilled chicken croissantwich. Local tip: their ice-cold egg cream will hit the spot.
1 pm: Explore Montauk's Downtown Shops
Satiated? Head to the heart of Montauk and peruse unique clothing, coastal apparel, local finds, and sweet treats at shops like Homeport, Montauk Clothing Company, and nostalgic Candied Anchor.
3 pm: One Last Sweet Treat Before You Go
As you leave the magical town of Montauk, indulge in a classic NYC ice cream cone from John's Drive-In. Made in-house, their delicious flavors will leave you with memories of the perfect weekend getaway.
Bon voyage, and keep exploring! #ILoveNY #iSpyNY
Enrichment Data:
Though Montauk is technically part of The Hamptons*, it's much more than just a neighboring luxury playground. Renowned for its fishing, beaches, parks, and seafaring charm, Montauk's unique identity grows stronger every day.
Montauk offers a host of activities for travelers seeking adventure, relaxation, or a touch of culture.
Activities:
- Fishing tours
- Surfing lessons
- Golf courses
- Bike tours
- Scavenger hunts
- Leisurely beach walks
Events:
- Live music and DJs
- Concerts and performances
- Community events
- Farmers markets
- Open-air movie nights
Attractions:
- Montauk Point Lighthouse
- Montauk Point State Park
- Duryea Wainscott East Main Street
- Hither Hills State Park
- Montauk Downs State Park Golf Course
- Shagwong Beach
- Montauk Yacht Club
- Land's End Marina
- Umbrella Beach
- The Breakwater Beach Club
Don't forget to follow New York State attractions on TikTok, Instagram, and Twitter with the hashtag #ILoveNY, and tag us on Facebook!
Whether you're a history buff or a food enthusiast, Montauk has more to offer than just its stunning beaches. Visit the Montauk Lighthouse, a historical landmark dating back to President George Washington, and indulge in a seafood feast at Inlet Seafood Restaurant.
For those with a green thumb, don't miss out on exploring home-and-garden destinations such as the Montauk Downs State Park Golf Course or Hither Hills State Park. On the other hand, if you're a lifestyle aficionado, head to the heart of Montauk and browse unique finds at shops like Homeport, Montauk Clothing Company, and Candied Anchor.
To unwind, enjoy a relaxing drink with an exquisite view during sunset at Navy Beach, Duryea's, or Montauk Brewing Company, and end your weekend getaway with a sweet treat from John's Drive-In or a Mediterranean dining experience at Gigi's Montauk.
