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a few fishing boats in the water at sunset near Chatham Inn

Exclusive Cape Cod Experiences

From whale-watching adventures to flights over the Cape in a vintage biplane, discover the best things to do in Cape Cod with exclusive experiences and private adventures by land, sea and sky. Back at the inn, a world of luxurious comfort awaits after the day’s discoveries.

A couple holding hands walking the shoreline of open water near Chatham Inn
Nearby Attractions

Local Experiences

Choose from a variety of curated local experiences to make your Cape Cod getaway unforgettable. From private whale-watching adventures to dune tours through the Peaked Hill Bars sand dunes, Chatham offers a wealth of activities to delight every guest.

A server hand holding a tray of cocktails at Chatham
Amenities

Hospitality at its Finest

Enjoy signature amenities, including on-site dining at Cuvée Bistro, welcome cocktails, afternoon tea, turndown service and everything you need for a carefree day at the beach.

Calendar of Events

Explore the best things to do in Chatham and across Cape Cod for a truly memorable visit.

  • Fresh Cape Cod cranberries at a Chatham farm stand
    Sep28

    Cranberries: From Cape Cod to American Icon

    Discover how the cranberry became an American icon through interactive exhibits that explore its deep roots in Cape Cod’s history, culture and landscape, from the Wampanoag people to the global legacy of Ocean Spray.

    Date: April 25, 2026 - October 18, 2026

    Time: Recurring daily

    Location: Heritage Museum & Gardens

  • A few people shopping at Falmouth Winter Farmer's Market
    Sep28

    Falmouth Winter Farmer's Market

    Check out the beloved market’s new location at Mullen Hall School.

    Date: Every Sunday

    Time: All Day

    Location: Mullen Hall School

  • Pumpkin People in the Park fall festival, Chatham, Cape Cod
    Oct12

    Pumpkin People in the Park

    Experience one of Cape Cod’s most beloved fall traditions as Pumpkin People in the Park transforms Chatham with whimsical, larger-than-life pumpkin displays created by local businesses, organizations and community members.

    Date: October 12 – 31

    Time: Recurring daily

    Location: Kate Gould Park

  • Oktoberfest beer steins near Chatham Inn, Cape Cod
    Oct17

    Oktoberfest

    Experience one of the Lower Cape’s favorite fall traditions at Chatham Oktoberfest, featuring festive entertainment, seasonal flavors and family-friendly fun for all ages.

    Date: October 17

    Time: 11:00 AM – 5:00 PM

    Location: Kate Gould Park

  • Caymus Cabernet Sauvignon from the wine list at Chatham Inn, Cape Cod.
    Nov12

    Caymus Vineyards Wine Dinner

    Journey to Napa Valley for an evening highlighting the rich, distinctive wines of Caymus Vineyards. Settle in for an intimate dinner where thoughtfully selected pours meet seasonal cuisine in the warm, elegant setting of Cuvée Bistro.

    Date: November 12, 2026

    Time: 5:30 pm - 9:00 pm

    Location: Cuvée Bistro

  • Cabernet Sauvignon bottle and glass of red wine at Chatham Inn, Chatham, Massachusetts on Cape Cod.
    Dec10

    Stags' Leap Wine Dinner

    Knock twice. Pour once. The Cellar Series concludes with Stags’ Leap Winery for an intimate, speakeasy-inspired evening of celebrated Napa Valley wines and thoughtfully crafted cuisine.

    Date: December 10, 2026

    Time: 5:30 pm - 9:00 pm

    Location: Cuvée Bistro

  • Santa visit during the holidays in Chatham, Cape Cod
    Dec11

    Christmas by the Sea

    A full weekend of small-town holiday traditions, shopping and family activities centered around Main Street in Chatham. Some events require tickets; others are open to the public and free to attend.

    Date: December 11 – 13

    Time: Recurring daily

    Location: Main Street and surrounding downtown Chatham, MA