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 – 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 & Drinks at Baleine in Dennis

Spend the evening at Baleine, Dennis Village’s stylish new wine bar from the team behind The Pheasant and Dunn & Sons Wine. The menu is built for lingering—fresh oysters, local seafood, crudo, steak tartare, artisanal cheeses, and other seasonal small plates—perfect alongside their thoughtful selection of natural wines, craft cocktails, and bubbly. With its warm lighting, curated vinyl soundtrack, and relaxed but elevated vibe, it’s an ideal spot for a cozy night out.

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

Spend a full day in Provincetown (Ptown), the vibrant, artsy tip of Cape Cod. Stroll Commercial Street for galleries, boutiques, and street performers, and stop by the Provincetown Art Association and Museum (PAAM) for an inspiring collection of local and national works. In the fall, the town’s creative energy feels even more intimate—perfect for browsing, people-watching, and soaking in the harbor views. 

Pro Tip: For a dose of history or adventure, climb the Pilgrim Monument for panoramic views, or hike out to the historic Dune Shacks.

Bonus Ideas & Seasonal Add-Ons:

  • Wellfleet OysterFest (mid-October) – A can’t-miss celebration of Cape Cod’s famous oysters, with shucking contests, live music, local food, and artisan vendors.

  • Fall Gallery Walks – Many Cape towns, including Ptown, offer special evening art strolls in September and October.

  • Autumn Whale Watches – Late-season trips offer a chance to see humpbacks before they migrate south.

  • Provincetown Tennessee Williams Theater Festival (late September) – A unique celebration of the playwright’s works and other bold performances.