Cape Cod in August is the definition of summer done right. The air is warm but breezy, the water is inviting, and the entire region buzzes with things to do, see, and experience. Locals know this is one of the best months to enjoy the Cape, not just for the weather but for the full calendar of festivals, food, music, and culture that make this stretch of New England feel extra special. If you’re heading to the Cape or already lucky enough to call it home for part of the summer, there are a few standout events you won’t want to miss.
Cape Cod Food Truck and Craft Beer Festival
Good food and cold drinks hit differently in the summer, and that’s exactly what this festival is all about. Held over a weekend in August, the Cape Cod Food Truck and Craft Beer Festival brings together thirty of the best food trucks from across New England. Whether you’re craving barbecue, wood-fired pizza, Korean spice, or cheesy comfort food, there’s something here that will leave you satisfied. The beer selection is just as impressive with over fifty local and national brews on tap. It’s the kind of event where you come hungry and leave full, maybe with a new favorite IPA or stout in hand. Lawn games, live music, and a relaxed vibe make this festival a favorite for families, couples, and groups of friends looking for a fun afternoon outdoors.
Annual La Tavola, Italian Fest Under the Stars
This isn’t your average community dinner. La Tavola transforms Steeple Street in Mashpee into a little slice of Italy, complete with a five-course meal, white tablecloths, and live music that sets the tone for a magical summer evening. Catered by Villaggio Ristorante, the menu always impresses with rich pastas, fresh salads, savory meats, and decadent desserts. You’ll be serenaded by Italian tenor Aaron Caruso and accordionist Corey Pesaturo while young performers from the local music academy add to the festive mood. The entire night feels like something out of a European postcard, with warm string lights overhead and the smell of fresh herbs and wine in the air. Locals look forward to this all year, and once you attend, you’ll understand why.
First Friday in Orleans
If you want a laid-back yet lively way to spend your Friday evening, Orleans delivers. First Friday is a town-wide celebration that brings together shops, artists, musicians, and restaurants to create a fun, walkable experience. From 5 PM to 8 PM, you can stroll through pop-up exhibits, catch a set by a local band, check out new art installations, or grab a drink at one of the town’s favorite spots. Businesses stay open late, offering special deals and a welcoming atmosphere. It’s a great way to get a taste of local culture and connect with the people who make Orleans such a special place to spend time in the summer.
Provincetown Carnival Week
Carnival Week in Provincetown is not just an event, it’s an experience. This weeklong celebration of LGBTQ+ pride and culture brings energy, joy, and creativity to every corner of town. From pool parties and dance nights to art shows and themed events, there’s always something happening. The highlight of the week is the Carnival Parade, drawing thousands of people dressed in colorful, over-the-top costumes as they make their way through the streets of Provincetown. Whether you’re part of the LGBTQ+ community or simply want to experience one of the most inclusive and vibrant weeks on the Cape, Carnival is an unforgettable way to celebrate summer.
Book Your Stay with Pretty Picky Properties
After a day of exploring Cape Cod’s best events, nothing beats coming home to a space that feels just right. At Pretty Picky Properties, we offer a wide range of vacation rentals that help make your Cape Cod experience effortless. From luxury homes with private pools to cozy pet-friendly cottages, our properties are located throughout the area including Brewster, Chatham, Wellfleet, and Dennis. Whether you’re planning a romantic escape or a family reunion, we have something that fits your needs and your style.
Our homes are designed to be more than just a place to sleep. Expect thoughtful touches, well-equipped kitchens, and outdoor spaces perfect for gathering. You’ll be close to all the action but tucked into neighborhoods that give you the peace and quiet you need to fully recharge. Booking with Pretty Picky means you’re working with a team that knows the area and wants your trip to be as seamless as possible.
Start Planning Your Vacation to Cape Cod in August
August is the Cape at its best. Whether you’re here for the food trucks, the music, the festivals, or just to soak in the summer vibes, Cape Cod has something for everyone. Let Pretty Picky Properties help you make the most of it with a vacation rental that fits the way you want to travel. Book your stay today!
