Montauk, NY Fall Weekend Itinerary

Montauk is one of my favorite fall escapes in the Hamptons. As the temperatures wind down the summer crowds thin out and the town takes on a cozier, more laid-back vibe — perfect for a weekend of exploring.

From state parks to boutique shops and waterfront restaurants, there’s plenty to love this time of year. Whether you’re visiting for a quiet couple’s weekend or a low-key getaway with friends, this itinerary has you covered.

I lived in the Hamptons for a year and regularly return to visit family, I put together this Montauk fall weekend itinerary based on some of my favorite things to do here during fall!

Montauk Fall Weekend Itinerary

Day 1

Montauk Point State Park & Montauk Point Lighthouse

Start your Montauk weekend at Montauk Point State Park, home to the iconic red-and-white striped lighthouse. As New York’s oldest lighthouse, it offers stunning views of the Atlantic Ocean and Block Island Sound — perfect for a morning stroll or photo op.

The grounds are scenic, and a walk along the rocky shoreline provides a beautiful introduction to the area, with the lighthouse visible from most trails. You can also visit the lighthouse museum and climb to the top for panoramic ocean views on clear days. There’s a small admission fee, but it’s well worth it when visibility is good.

If you’re visiting in November, keep an eye out for seals, which frequent the area from November through April. The Seal Haul Trail is your best bet for spotting them up close.

Camp Hero State Park

Just a short distance from Montauk Point, Camp Hero State Park offers dramatic bluff-top views and the eerie ruins of a former military base that inspired the Netflix hit, Stranger Things.

If you’re into spooky legends and offbeat history, this is the spot. The park’s lore is so compelling that the original concept for the Netflix series was set in Montauk and even titled Montauk before morphing into the version of Stranger Things we know today.

Whether you’re drawn by the backstory, the coastal views, or the chance to explore something that feels very un-Hamptons, Camp Hero is one of my personal favorites.

Best of all, if you’ve already paid to park at Montauk Point State Park, you can visit Camp Hero the same day for free.

For more, check out Top Things To Do In Camp Hero State Park.

Browse The Shops Downtown

Next, head into downtown Montauk, a compact and walkable area that’s perfect for browsing. You’ll find a fun mix of boutique shops, beachwear, surf gear, and vintage treasures. I love places like Wyld Blue Montauk, Homeport, and Montauk Vintage — but honestly, it feels like I discover a new favorite every time I visit.

Take your time wandering in and out of shops, then fuel up on caffeine or a bite at favorites like Left Hand Coffee, Montauk Bake Shoppe, Joni’s, Streetfood on the Green, Round Swamp Farm, Bambi’s Cafe, or Naturally Good.

Grab A Drink From Montauk Brewing Company

After exploring downtown, walk over to Montauk Brewing Company for a local craft beer.

Housed in a small red barn in the heart of town, the taproom serves rotating lagers, IPAs, and ambers brewed entirely on-site. If the weather’s nice, grab a seat on the patio to relax and enjoy the sunshine while sampling some local favorites.

Dinner On The Water

For dinner, Montauk has no shortage of restaurants with great views — the town has some of the best waterfront restaurants in the Hamptons, in my opinion!

Consider dining at The Montauket, Mavericks, The Harvest on Fort Pond, or Gosman’s, where you can enjoy casual, coastal fare while watching the sun set over the water.

If the weather’s on your side, outdoor seating is perfect for sunset views. But even on a cold day, most spots offer cozy indoor spaces — and some feature live music in the evenings too.

Note: Many Montauk restaurants are seasonal, but the ones listed above are typically open in the fall. That said, it’s always wise to double-check hours before heading out (calling is best!), as things can change!

After Dinner Drinks

If you’re looking to keep the night going, Montauk’s bar scene is lively and fun even in fall.

Popular spots include Shagwong, TAUK, The Dock Bar & Grill, or Montauket. Whether you want a laid-back cocktail or a bustling music scene, there’s something for everyone.

Day 2

I’ve included quite a few options for Day 2, depending on weather and personal preference.

Brunch

Start the day with brunch at Anthony’s Pancake & Waffle House (cash only!), a beloved Montauk staple that’s been serving hearty breakfasts since the ’50s. Think fluffy pancakes, waffles, eggs, and home fries. It’s a local favorite for a reason, especially if you’re craving a traditional diner-style breakfast.

If you’re in the mood for something lighter and more modern, head to Mostrador Marram, located at the Marram Montauk hotel. Their brunch menu features dishes like grain bowls, fresh fruit, and smoothies, served in a beautifully minimalist beachfront setting. (Note: Mostrador Marram typically closes for the season in mid-October — double check before heading out!)

Option 1: Visit The Beach

If the weather is nice, head to Ditch Plains Beach after breakfast. This is one of the most fun and iconic beaches in the Hamptons, well known for its surf scene. Even in the fall, it’s a peaceful place for a walk along the ocean — and a great spot for people-watching

Bring a hot drink, bundle up, and enjoy the wide stretch of sand. In early fall, you might even catch a glimpse of dolphins or whales just offshore.

Keep in mind: a beach parking permit is required year-round, and most beaches only accept a Town of East Hampton or Resident Town Permit. Kirk Park Beach and South Edison Beach are the only town beaches that offer day passes.

To skip the parking hassle altogether, consider biking, walking, or getting dropped off. Remember, parking requires a permit, but the beaches themselves are free and open to everyone. Both Kirk Park Beach and South Edison Beach are centrally located near downtown and easy to walk to.

Regulations can change from year to year, be sure to check the latest rules at East Hampton Beach Parking Permits (non-resident) before you go. Also, your hotel will likely have up-to-date beach access information.

Option 2: Spa Day or Horseback Riding

If it’s not quite beach weather, you’ve got a few alternative options.

Book a treatment at Gurney’s Montauk Resort & Seawater Spa, one of the only oceanfront spas in the Hamptons. The grounds are stunning and the indoor seawater pool is perfect for a chilly day.

If the weather isn’t too bad and you’re up for something more active, Deep Hollow Ranch offers scenic trail rides through quiet parts of Montauk — a unique and memorable experience especially in fall when the leaves are changing.

Option 3: Afternoon Day Trip To A Nearby Hamlet

Whether you spent the morning at the beach, horseback riding, or relaxing at the spa, a visit to a nearby Hamptons hamlet is a great way to spend the second half of your day.

Just keep in mind: Montauk is fairly removed from the other towns, so a day trip will require a bit of planning.

The closest options are East Hampton and Amagansett, both are great for boutique shopping, art galleries, and a stroll down Main Street. East Hampton leans more upscale with luxury boutiques, while Amagansett is a little more low-key and local (it’s also home to one of my favorite Hamptons farm stands, Amber Waves!).

If you’re willing to venture further, consider:

• Sag Harbor – Known for its charming harbor, historic architecture, and vibrant Main Street. It’s full of personality and has a deep whaling history. For a full guide, check out my Sag Harbor Day Trip Itinerary.
• Southampton – Offers a classic New England feel with beautiful homes, excellent museums, and a polished town center. I’ve got a full day trip guide at One Day In Southampton, NY.
• Wölffer Estate – Ideal for a fall wine tasting with vineyard views and a cozy atmosphere. The main tasting room requires a reservation, but their more casual Wine Stand is open to walk-ins. It’s mostly lawn seating with a few tables, and on weekends they often host sunset live music (yes, even in fall… find the schedule at Wölffer Estate Happenings).

If you are planning to visit another hamlet, I highly recommend grabbing food on your way in or out of town at Lobster Roll (LUNCH). It’s iconic for a reason — casual, quick, and home to one of the best lobster rolls on the East Coast. You can’t miss it, just look for the the giant “LUNCH” sign.

Dinner

For your final night, you’ve got a few great dinner options. If you ventured out to another hamlet, consider grabbing dinner there — each one has solid year-round restaurants worth checking out.

Prefer to stay local? Back in Montauk, some good choices include Inlet Seafood Restaurant & Sushi Bar, Alimentari Beach Montauk, or Bird on the Roof.

Bonus Fall Activities To Consider

Here are a few fall-specific activities that would round out the itinerary nicely:

• Seal Watching at Montauk Point State Park (especially in late fall).
• Walking Dunes Trail in Hither Hills – the shifting sand dunes are gorgeous in fall, and the crowds are minimal.
• Fall Foliage: Take a scenic drive along Old Montauk Highway — the combination of ocean views and fall color is lovely.
• Montauk Fall Festival – If your trip aligns, this popular mid-October event includes live music, local vendors, beer tents, and a famous clam chowder contest.

If you’re looking for more fall things to do, check out Fall In The Hamptons: Top Things To Do.

Where To Stay In Montauk In Fall

Montauk has one of the widest ranges of hotels in the Hamptons, from simple beach motels and charming boutique hotels to larger resort-style properties. It’s also one of the only places in the Hamptons where you’ll find true beachfront hotels.

This time of year you’ll find guest rooms at lower prices than peak season — definitely a large perk of visiting during the fall months!

A few popular hotels in Montauk include:

• Luxury: Gurney’s Montauk Resort & Seawater Spa
• Mid-range: Hero Beach Club
• Budget-friendly (by Montauk standards): Daunt’s Albatross

For more details and additional hotel recommendations, check out The Best Hotels In Montauk.

Montauk Weather In Fall

Montauk’s weather will play a big role in how your fall weekend unfolds, which is why I included so many options in this guide.

Generally speaking, fall weather in the Hamptons is mild, with plenty of sunny days and about seven days of rain per month.

That said, it’s still hurricane season. Even if Montauk isn’t directly impacted, storms along the East Coast can bring several days of heavy rain to the region.

Also keep in mind that Montauk tends to be cooler than the rest of the Hamptons, thanks to its location at the very tip of Long Island, surrounded by water. Heavy fog is also common, especially in the early morning and evening.

Below are the average monthly temperatures for fall in Montauk:

• September – 71° / 64°F (High / Low)
• October – 63° / 55°F
• November – 54° / 45°F

What To Wear In The Hamptons In Fall

As mentioned above, fall in Montauk can be a bit unpredictable — sunny and warm one moment, foggy and cold the next — so packing layers is key.

Here’s what I recommend bringing:

• Lightweight layers – Think long-sleeve tees, lightweight sweaters, and a denim or utility jacket you can throw on when the temps drop.
• Comfy jeans or leggings – Great for walking around town or heading out on a coastal trail.
• Something cozy for the beach – A fleece or oversized hoodie is perfect for beach strolls.
• Casual dinner outfit – Montauk is stylish but not overly dressy. A cute knit dress or jeans with a nice top works well just about anywhere.
• Comfortable shoes – Bring sneakers or boots for exploring parks, plus sandals or slip-ons if it’s still warm during the day.
• A beanie or scarf – It can get windy near the water!
• Swimsuit (just in case) – If you’re heading to Gurney’s spa or hitting a hot tub, you’ll be glad you packed it.

And don’t forget sunglasses and SPF — even in fall, the sun off the water can be bright!

Getting To Montauk

Montauk is located at the eastern tip of Long Island, making it a bit of a trek from New York City but well worth the journey. By car, it’s about 3 – 4 hours from Manhattan, depending on traffic. The drive along scenic Montauk Highway (Route 27) is especially beautiful in the fall, and traffic tends to ease up as the season goes on.

Tip: Download directions ahead of time — cell service can be spotty on the East End. And be sure to fill up your tank before you reach the Hamptons, gas stations are few and far between and tend to get crowded on weekends.

One of the most convenient ways to get to the Hamptons is via the Hampton Jitney, a luxury bus liner with many routes between Manhattan and the Hamptons. Transit time is about 3 – 4 hours in each direction. Just be aware, not all bus routes stop in Montauk. 

Train service is available via the Long Island Rail Road (LIRR). The Montauk Branch departs from Penn Station and takes roughly 3.5 – 4 hours to reach Montauk. Book early if possible, especially in early fall.

The Viking Fleet offers fast ferries from New London, CT or Block Island, RI to Montauk. The seasonal ferry runs until about mid-October.

For the quickest (and least affordable) option, BLADE offers helicopter service into Montauk. Think commercial airline but helicopter, it may be pricey but it’ll get you to Montauk in a fraction of the time.

For those flying in, Long Island MacArthur Airport (ISP) in Islip is the closest airport, about 1.5 hours west of Montauk. From there, you can rent a car or take a combination of shuttle services and taxis to reach the town.

For more information, check out How To Get To The Hamptons.

Getting Around Montauk

While Montauk is more walkable than many other Hamptons towns, you’ll need a car if you want to explore beyond the downtown area. Shops, restaurants, and beaches are within walking distance of each other, but reaching places like Montauk Point Lighthouse or the marina on Lake Montauk requires a longer ride.

There are no traditional rental car companies in Montauk, so it’s best to rent a car before you arrive. However, carshare companies like Turo may be available.

Uber and Lyft are available in the area, but wait times can be unpredictable — especially in fall. For a more reliable option, Montauk Taxi is a local cab service worth trying.

Getting around by bike is a great way to explore at a slower pace when the weather is nice. Montauk Cycle Company and Montauk Surf & Sports both offer standard and electric bike rentals. Reservations are recommended.

Fall is a wonderful time to visit Montauk — free of summer crowds and full of peaceful charm. While seasonal closures can make logistics a bit trickier, the quiet beauty and slower pace make it well worth the effort.

I hope you’ve found this helpful in planning your trip and have the best time!

Any questions? Please leave a comment below or reach out on social media.

Looking for more ideas? Check out my additional Hamptons and New York guides below.

More Information For Your Trip To Montauk:

• Fall In The Hamptons: Top Things To Do
• Best Things To Do In Montauk
• Montauk Day Trip Itinerary
• Top Things To Do In Camp Hero State Park
• Top Hotels In Montauk
• All Montauk Guides

More Information For Your Hamptons Vacation:

• Hamptons Travel Guide (everything you need to know!)
• Amagansett Guides
• East Hampton Guides
• Sag Harbor Guides
• Southampton Guides
• All Hamptons Guides

More Information For Your Trip To New York:

• North Fork Guides
• Long Island (Central) Guides
• New York City Guides