Cape Cod Arts & Culture Itinerary

IMMERSE YOURSELF IN CAPE COD’S CREATIVE SPIRIT WITH THIS CULTURE-LOVER’S DREAM ITINERARY. FROM GALLERIES AND HISTORIC THEATERS TO GARDENS, LIVE MUSIC, AND FESTIVALS, YOU’LL EXPERIENCE THE CAPE THROUGH ART, HISTORY, AND PERFORMANCE—ALL WHILE EXPLORING ITS MOST CHARMING TOWNS.

DAY 1: Dennis & Harwich – Arts Complex & Local Theater

Morning:

Cape Cod Museum of Art (CCMA) – Start your day exploring regional and contemporary art at the Cape Cod Museum of Art. Don’t miss their sculpture garden and rotating exhibitions celebrating the Cape’s creative legacy.

 

Midday:

Lunch in Dennis Village – Try Scargo Café or the Mercantile for something casual and local.

 

Afternoon:

Cape Cod Playhouse & Cape Cinema – Catch a matinee at the historic Cape Cod Playhouse (America’s oldest professional summer theater) or explore the beautifully designed Cape Cinema, known for its hand-painted ceiling and indie film lineup.

 

Evening:

Harwich Junior Theatre (Cape Cod Theatre Company) – Wrap up the day with a live performance in Harwich. This community-focused theater offers family-friendly productions and classics alike in an intimate setting.

Pro Tip: Check the schedule in advance—shows sell out quickly during the summer.

DAY 2: Sandwich & Hyannis – History, Music & Iconic Venues

Morning:

Sandwich Glass Museum – Step back in time and watch live glassblowing demonstrations while learning about Sandwich’s role in American glass history. It’s part museum, part immersive art experience.

 

Afternoon:

Heritage Museums & Gardens – Explore 100 acres of gardens, art, and Americana, including an antique car collection and rotating exhibitions. A must for lovers of history, nature, and design.

 

Evening:

Dinner in Hyannis + Live Music

Dine downtown, then catch Hyannis Sound, Cape Cod’s beloved all-male a cappella group. Their harmonies and humor make for a light-hearted, unforgettable show.

Pro Tip: Shows take place in churches and town halls—check their summer tour schedule!

Day 3: Provincetown Day Trip – The Creative Soul of the Cape

The Entire Town of Provincetown (Ptown) – Spend a full day soaking in Ptown’s vibrant arts scene. Walk Commercial Street for galleries, street performers, and pop-up shows. Visit the Provincetown Art Association and Museum (PAAM), and maybe even catch a drag show or experimental theater performance in the evening.

Pro Tip: Visit the Pilgrim Monument or walk to the Dune Shacks if you’re feeling adventurous.

Bonus Ideas & Seasonal Add-Ons

  • Melody Tent (Hyannis) – A summer staple offering big-name concerts in an intimate round tent setting. If there’s a show during your stay, don’t miss it!
  • Festivals to Look For:
    • Love Live Local (LLL) – Celebrates local makers and creatives, held seasonally in Hyannis.
    • Cape Cod Hydrangea Festival (July) – Self-guided garden tours and floral events across the Cape.
    • Outer Cape Music Festival – A summer highlight showcasing local and regional musicians in unique venues.
    • Woods Hole Film Festival (late July–early August) – One of the best indie film festivals in New England, with screenings and panels in a charming scientific village.