Your Creative Weekend on Cape Cod Starts Here

Curated by Pop Up Street Cape Cod

Cape Cod has much more to offer than only beaches and seafood spots. It has local art, live music, hidden creative spaces, community events, coastal mornings, late-night conversations, and meaningful experiences shared with the people you love.

Whether you’re planning a girls’ getaway, birthday trip, creative retreat, or weekend escape, Pop-Up Street helps you experience the creative side of Cape Cod through curated experiences woven naturally into your stay.

Thursday — Arrive & Connect

Check into your Airbnb or vacation stay and settle into the slower rhythm of Cape Cod.

Join us for Canvas Connections, our once-a-month creative social paint experience where locals and visitors gather for art, conversation, music, and connection. It’s the perfect way to ease into the weekend while meeting people and experiencing the local creative community.

Afterward, explore Main Street Hyannis for cocktails, dessert, live music, or a late-night walk through town.

Friday — Explore the Town

Start your morning with coffee from a local café like Chez Antoine Cafe, before spending the day exploring beaches, boutiques, galleries, bookstores, and hidden corners of Cape Cod.

Spend the afternoon relaxing at your Airbnb, heading to the beach, or discovering local events happening around town.

In the evening, gather your group for a private creative experience brought directly to your vacation stay. Whether it’s painting, candle making, or another curated activity, the experience is designed to create connection, laughter, and unforgettable memories together.

Finish the night with dinner, rooftop drinks, live entertainment, or a cozy night in.

Saturday — Beach Days & Coastal Nights

Sleep in, grab brunch, and spend the day enjoying Cape Cod your way.

Visit local beaches, take a boat tour, shop small businesses, attend local festivals and markets, or simply slow down and enjoy the atmosphere of the Cape.

As the sun sets, enjoy another curated evening experience — from intimate gatherings and creative workshops to private dinners and celebration moments with your group.

Cape Cod weekends are meant to feel easy, inspiring, and memorable.

Sunday — Slow Mornings & Lasting Memories

Wrap up the weekend with a slow brunch, beach walk, coffee run, or private chef experience at your Airbnb before heading home refreshed and inspired.

The best weekends aren’t packed with schedules — they’re filled with meaningful moments, creativity, connection, and experiences you’ll remember long after vacation ends.

Curated Experiences Available

Canvas Connections

Our creative social paint experience bringing locals and visitors together through art, music, and conversation.

Private Paint Experiences

Relaxed creative gatherings brought directly to your Airbnb or private residence.

Private Candle Making

A cozy hands-on experience perfect for girls’ weekends and celebrations.

Baby Arrival Paint Parties

Create wearable keepsakes while celebrating a new arrival.

Culinary Experiences

Private chef dinners and curated food experiences designed for memorable gatherings.

Perfect For

• Girls’ Weekends

• Bachelorette Trips

• Birthday Getaways

• Couples Escapes

• Creative Retreats

• Family Gatherings

• Vacation Groups

Your weekend starts here.