Two people are enjoying a bike ride on a sunny day near a white fence and the ocean, with wicker baskets on their bikes.

The Ultimate Fall Weekend in Chatham: A 3-Day Itinerary

While each guest’s stay is customized based on their individual interests, we offer the following three-day sample itinerary to highlight some of our favorite activities and can’t-miss experiences for an unforgettable visit to Chatham Bars Inn. Our Concierge team is here to help create a personalized itinerary, so you can make the most of your stay.

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Day 1

8am     Start your day with a delicious breakfast in STARS with expansive views of the ocean from 9-foot floor to ceiling windows - don’t miss the Lobster Benedict and the French Toast Bread Pudding.

10am    Biking or Museums: Borrow bikes for a casual ride to the Chatham Light lighthouse, featured in the Disney movie “The Finest Hours”, or along the extensive Cape Cod Rail Trail. For an indoor activity, reserve in advance to visit the nearby Atwood House Museum or Chatham Marconi Maritime Center.

1pm       Enjoy fall boating as you cross Aunt Lydia’s Cove on our complimentary BarTender shuttle boat to walk along the undisturbed North Beach Island or plan ahead for a morning or late day seal/harbor tour or a private whale watch excursion.

7pm      Dine on The Veranda – enjoy an offshore breeze with stunning views of Chatham Harbor and treat yourself to guest favorites: Porterhouse Steak for Two, Lobster Rigatoni, or Seared Scallops.

Day 2

8am      Enjoy breakfast in your room or on your deck from our In-Room Dining menu.

10am    Play a game of tennis on our Har-Tru clay courts or take a stroll on our private beach to the Chatham Fish Pier.

11am     Swim in the heated pool or relax in a poolside cabana.

1pm      Enjoy lunch at the Beach House Grill, don’t miss the famous Lobster Nachos and our signature Watermelon Margarita.

3pm       Take a 5-minute stroll to Chatham’s Main Street to explore the unique shops and galleries. Or ask at the Valet stand for a complimentary ride to and from Main Street as part of our Lexus partnership.

4pm       Venture just off Main Street to Chase Park to see the Godfrey Windmill which was built in 1797 and the Chatham Labyrinth, a replica of a medieval labyrinth found in a cathedral in France.

6pm      Enjoy a drink at the South Lounge Bar and try our Cape Sling, made in one of only ten Imperial Shakers in the world. Take a turn at the wheel and mix your cocktail yourself!

7pm      Dine in our Sacred Cod Tavern. Begin with a cocktail crafted from one of our signature spirits, then enjoy our classic Parker House Rolls along with a Lobster Roll, Fish & Chips, or the Sacred Burger.

A white church with a tall steeple surrounded by numerous pumpkins, set amid trees under a clear blue sky.
A garden with vibrant flowers, a gravel path, and tents; lush greenery and trees under a blue sky complete the serene scene.

Day 3

8am      Breakfast on The Veranda – enjoy Pavlova Waffles, Lobster and Grits, Farm Pisto Manchego and more, all while taking in the stunning views.

10am    Visit our luxurious full-service spa for a massage in an outdoor cabana in the spa’s Zen Garden, spend some quiet time in the peaceful relaxation room or indulge in one of the spa’s specialty treatments such as the Endless Essence Massage or the Elevated Elixir Body Scrub and Facial.

1pm       Stop to browse at the signature shop in the lobby. Some of our favorite gifts are Bella Tu dresses, cashmere wraps and Chatham Bars Inn logo quarter-zips.

2pm     Explore the great outdoors at the nearby Monomoy National Wildlife Refuge or take a ride to Wellfleet’s Marconi Station and White Cedar Swamp Trail, part of the Cape Cod National Seashore

Fall in Chatham is an invitation to slow down, explore at your own pace and enjoy the beauty of Cape Cod without the summer crowds. From coastal walks and local shops to seasonal dining and scenic adventures, there is plenty to discover.

Make Chatham Bars Inn your home base for a fall getaway and enjoy a weekend filled with coastal scenery, local experiences and time to simply relax and take in the season.

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Forbes Travel Guide Five Star Hotel, recognized once again among the world’s finest hotels

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#1 Resort in Massachusetts in the 2025 Condé Nast Traveler's Readers' Choice Awards

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#1 Best Waterfront Hotel/Resort in the USA TODAY 2026 10Best Readers' Choice Travel Awards

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#1 Best Waterfront Restaurant in the USA TODAY 2025 & 2026 10Best Readers' Choice Travel Awards – Beach House Grill

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Forbes Travel Guide 2025 Hotel Icon. Recognized as one of 6 hotels in the US and 23 hotels worldwide.

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