Montauk in the offseason: Experience 'The End' like a local

Locals call it "The End," and in winter, that nickname takes on a literal charm in Montauk: empty beaches, quiet streets and the Atlantic stretching endlessly against the horizon. Unlike the polished Hamptons just up the road, Montauk retains its fishing-town grit and a community rooted in tradition. Offseason, the town sheds its summer frenzy and reveals itself in all its rugged, authentic glory.

With more than 5,000 acres of parks and protected coastline, Montauk is an outdoor playground year-round. From hiking and surfing to fishing and winter golf, the natural beauty and authentic experiences don’t stop when the tourists leave. The offseason isn’t just a slower time of year — it’s when Montauk comes alive for those willing to explore it on its own terms.

This is the season to experience Montauk as locals know it.

Holiday magic and seasonal deals

Few places capture that seasonal charm better than Daunt’s Albatross Motel, a third-generation, family-owned inn that has welcomed guests year-round for nearly five decades.

"Rooted in what my grandpa believed, that’s what we’ve done since 1976," says Leo Daunt, owner and general manager. "If you ran a business in Montauk, you opened when it was busy and stayed open when it was slow. The locals need a place to go too, not just tourists." Today, the inn blends timeless beach-town charm with handcrafted, modern touches, from antique furniture in each of the 24 guest rooms to the warm, inviting atmosphere that makes the offseason feel special. And yes, Koda, the family golden retriever, is on hand to greet you at check-in.

Winter is the perfect time to visit: Igloos provide a cozy retreat, and across the street, the hotel’s restaurant, Bird on the Roof, transforms into a holiday pop-up with whimsical decorations and a festive prix-fixe menu. The inn’s Holiday Stay & Supper package — two nights at Daunt’s plus a three-course dinner for two with a bottle of wine — starts at $500, offering a rare chance to enjoy the season in style and comfort. Book online.

The town itself joins in the festivities. The Chamber of Commerce awards the best-decorated businesses, and Bird on the Roof has taken home the prize five years running. The Montauk Christmas Festival (Dec. 13-14) brings music, reindeer from Buffalo, train rides for kids and a lively holiday atmosphere on the town green, making winter in Montauk feel cozy and magical.

Cozy escapes and wellness

For a luxury escape, few places match Gurney’s Montauk. Prices drop dramatically in the offseason compared to the summer, with stays starting at $350 in December. Guests can reserve oceanfront igloos and take in panoramic views of the Atlantic with an exclusive menu of bites transformed for winter comfort, like the spicy, red angry lobster roll. 

The igloos can be reserved for up to six people for a $50 fee that is donated to local charities; a $200 minimum applies. On weekends, the indoor pool transforms into a "dive-in ,"movie theater that plays children's movies for a family-friendly activity free for guests.

For both guests and nonguests, the spa at Gurney's operates year-round, with winter weekday specials, including a $190 facial and 60-minute massage. Booking a treatment includes access to the bathhouse, where visitors can soak in the cold plunge, hot plunge, steam room and sauna. The hotel's new restaurant, GiGi's, opened this past season and offers a $65 three-course prix-fixe winter menu Sunday through Thursday.

Eat like a local

No visit to Montauk is complete without seafood, and Bennett Shellfish delivers a taste of local tradition with its legendary two-for-$38 lobster roll deal, complete with a bag of potato chips. The shop is run by Clint Bennett, a 14th-generation East End bayman, and his wife, Kimberly.

"One day I said, what can I do to give the people something of the past ... something affordable and something good," Clint said. "If the prisoners could have eaten lobster back in the day, why can’t people enjoy it now without feeling like they have to empty their bank account?"

The counter is small and cozy, tucked inside the Bennett home, and everything is served to go. Park in the Bennetts' driveway, head inside and carry your lobster rolls straight to the Montauk Lighthouse, New York State’s oldest lighthouse, built in 1796.

Outdoor adventures and scenic trails

Montauk surprises even seasoned visitors with its abundance of natural beauty. Hither Hills State Park has more than 10 miles of trails through oak, shadbush, olive and pine forests, opening onto bluffs and beaches with sweeping ocean views. The park includes Native American stone house ruins and Seal Haulout Trail, where seals can often be spotted sunning on rocks in winter. The Walking Dunes, reaching up to 80 feet, are a striking testament to centuries of wind and sand sculpting the landscape.

Camp Hero State Park, spanning 425 acres, offers wooded trails, dramatic cliffs and beaches reminiscent of Big Sur. History and nature intersect here: The former military installation is rumored to have inspired Netflix’s ''Stranger Things.'' Trails lead to the radio tower or lighthouse, with fewer crowds if you arrive after 4 p.m.

For the adventurous, winter surfing lessons at Corey's Wave and East End Surf Club are available starting at $150, or skip the dip and watch the pros at Ditch Plains and Shadmoor State Park. Montauk Downs, one of New York’s top public golf courses, which is open year-round and offers offseason tee times starting at $32 and $22 after 1 p.m. Seniors can play for $22 or $17 during twilight hours on weekdays and juniors aged 17 and under can play for the same prices throughout the week. Non-residents pay $55 or $39 twilight. To make a reservation online, there's an additional $5 fee.

Sunset and evening magic

The day winds down at The Montauket, a 1960s fishing lodge-turned bar and restaurant. In winter, crowds are minimal, leaving only a handful of people to enjoy the glow of a Fort Pond Bay sunset. It’s an intimate, unforgettable way to take in the town’s natural beauty.

Montauk offseason is quiet, cozy and richly layered. From holiday events and igloos to lobster rolls, hiking, surfing and sunsets, it offers experiences unavailable during the summer crush.

"If you’re still looking for that old-school, quiet Montauk that’s undiscovered, talk to the locals, take your time and you could get cool deals," Daunt says. In winter, there’s nothing better than following that advice.