3 Perfect Cape Cod Days at Chatham Bars Inn

3-Day October Itinerary at Chatham Bars Inn

While each guest’s stay is customized based on their own interests, we offer the following 3-day sample itinerary to highlight activities, events and “can’t miss” experiences for an unforgettable October visit to Chatham Bars Inn. We look forward to welcoming you to Cape Cod’s Most Beautiful Address!


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 Frittata and Austin’s Avocado Toast.

Biking or Museums: Borrow bikes from our Bike Shop (until Columbus Day) 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

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.

Dine in our classic South Lounge by the cozy fireplace. Start with a “Blame it on the Bourbon” cocktail featuring our own specialty Chatham Bars Inn Maker’s Mark bourbon or a cranberry-inspired “Never Bog Down” mocktail followed by a Lobster Roll, Fish & Chips DryAged Prime Burger


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

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

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

Enjoy lunch at the Beach House Grill on the deck or with your toes in the sand, don’t miss the famous Lobster Nachos and our own signature “Coastal Encounter” beer.

Take a 5-minute stroll to Chatham’s Main Street to explore the unique shops and galleries. A few of our favorites are Candy Manor, Gallery Antonia, Yankee Ingenuity, Sundance Clothing, Mahi Gold, Struna Gallery and Gustare Oils & Vinegars. If you prefer not to walk, just ask at the Valet stand for a complimentary ride to and from Main Street as part of our Lexus program.

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.

Experience creative cocktails prepared tableside at our new STARS Mixology Lounge, try the Biondo Manhattan or Charles Hardy Soda accompanied by our Lobster Toast and Duck Fat “Cracker Jack’s”.

Dine at our signature STARS restaurant, our favorites include the Tomahawk Ribeye for Two, Seared Tuna, Local Catch and Brown Butter Gnocchi.


Breakfast at STARS – treat yourself to guest favorites Caramelized Banana Brioche French Toast and Cranberry Buttermilk Pancakes.

Visit our luxurious full-service award-winning spa for a massage in an outdoor cabana in the spa’s Zen Garden, spend some quiet time in the newly-renovated relaxation room or indulge in one of the spa’s specialty treatments such as the Espresso Mud Detoxifying Scrub or Healing Seaweed Body Wrap.

Stop to browse at the signature shop in the lobby. Some of our favorite gifts are Adina Reyter jewelry, cashmere wraps, Chatham
Bars Inn logo quarter-zips and baseball caps.

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.

Additional October Ideas and Events

Oct 1 – 31 Visit the Farm Stand at our 8-acre Chatham Bars Inn Farm in Brewster
Oct. 3 - Pig & Whiskey Dinner at Chatham Bars Inn Farm
Oct. 3 – 4 - Orvis Fly Fishing School at Chatham Bars Inn
Oct. 9 and 10 - Harvest Wine Dinners at STARS
Oct. 18 - Veuve Clicquot Champagne & Oyster Tasting at STARS
Oct. 16 – 31 - Pumpkin People in the Park at Kate Gould Park, Main Street Chatham
Oct. 23 and 24 - James Beard “Flashback” Dinners at STARS
Oct. 30–Nov. 1 - Seaside “Not-So-Scary” Halloween Family Weekend at Chatham Bars Inn

*Please note: Pool Cabanas and Beach House Grill are open through Oct. 12; boating is
weather dependent and available through Oct. 31; bikes are available at the Bike Shop until Columbus Day. Advanced reservations for spa treatments are highly recommended.

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