Girls Guide to Chatham, Cape Cod
Chatham is a quintessential seaside New England town and my personal favorite spot on the Cape. It seamlessly blends classic New England charm with upscale flair. The Main Street is full of picturesque boutique shops and top-tier restaurants. It’s the perfect place for a leisurely afternoon of shopping and people-watching. Beyond Main Street there is cottages with dreamy porches overlook the ocean and gardens bursting with hydrangeas. There’s so much to do and see here, once you’ve been to Chatham you’ll understand why it feels like the opening credits to the best kind of summer story, a real-life set of The Summer I Turned Pretty.
Where to Stay:
Chatham Bars Inn – This iconic oceanfront resort is full of storybook cottages and private beach cabanas perfect for lounging in style. Sip cocktails by the pool, lounge on the Adirondack chairs overlooking the harbor, and indulge in seaside fine dining—every part of this resort feels like a slice of summer magic. Wander along the private beach at sunrise, stroll through the manicured gardens dotted with hydrangeas, or unwind at the spa with ocean-inspired treatments. Whether you’re taking a sunset sail, enjoying fresh seafood on the terrace, or simply curling up with a book by the water, Chatham Bars Inn feels like your own real-life summer dream.
Wequassett Resort and Golf Club – Just outside Chatham on the sparkling waters of Pleasant Bay, this five-star retreat is pure perfection. Picture charming waterfront cottages, an award-winning golf course framed by lush greenery, and sunsets that turn the bay into liquid gold. Whether you’re savoring fresh seafood on a terrace overlooking the water, teeing off in serene elegance, or simply strolling the manicured grounds, Wequassett offers the perfect blend of luxury, leisure, and that unmistakable Cape Cod magic.
What to do:
Seal-spotting at the Chatham Fish Pier – Watch these cuties pop up from the water, the perfect mix of adorable and mesmerizing.
Live summer concerts at Kate Gould Park – Local tunes make the perfect soundtrack to a golden afternoon on Main St.
Boating adventures with Down Cape – Enjoy the sparkling coastline the best way, by boat.
Beach day at Lighthouse Beach - Walk the sandy beach, hunt for seashells, and swim in the ocean.
Picnic on the beach- Swith Coastal Picnic Cape Cod -They carefully curate your perfect picnic for you and your friends!
Shop on Chatham’s Main St. – Wander past coastal storefronts, pick up seashell treasures, and enjoy the coastal charm.
Catch the sunset at Chatham Bars Inn – Lounge in an Adirondack chair with a glass of wine as the sky drapes itself in a cascade of color, the perfect ending to a dreamy day.
Where to Shop:
A perfect afternoon in Chatham is spent wandering through boutiques brimming with hydrangea-themed treasures and coastal tchotchkes. Main Street is lined with charming shops, galleries, and specialty stores that make you feel like you’ve stepped into an old-time New England storybook town. From preppy classics like Apres Sea to fun local classics like Beach Bum Surf Co. Main Street has everything you need for while shopping on the Cape. Here’s a list of my favorite Chatham shops:
Apres Sea- A chic new boutique on Main Street with trendy clothes and accessories that capture the Cape Cod summer vibe.
Chatham Home – For coastal-chic home decor, pillows, glassware, and art pieces that bring Cape Cod charm into your home.
Beach Bum Surf Co. - Just steps from the beach, this vibrant boutique by local designer Candace Bouffard offers surf-inspired apparel and accessories for men and women, from cozy hoodies to vintage denim it’s the perfect place to shop to embrace the coastal lifestyle.
Mural Gallery & Local Art Shops – Chatham has a thriving art scene, with plenty of galleries showcasing photography and nautical-inspired pieces.
Cape Shark- locally owned boutique in Chatham, Massachusetts, offering a range of apparel and accessories inspired by Cape Cod's coastal charm!
Chatham Candy Manor – An old-fashioned candy shop famous for fudge, chocolate-dipped everything, and nostalgic sweets.
Where to Dine:
Evenings in Chatham call for oysters and lobster paired with a crisp glass of wine at sunset. Whether you’re a local grabbing a bite before a baseball game at Veterans Field or a traveler on the hunt for your next favorite meal, here’s my roundup of the best spots to dine in town.
The Veranda at Chatham Bars Inn- Enjoy fresh, local seafood and farm-to-table dishes with sweeping views of the Atlantic. Their oceanfront terrace is as classic Cape Cod as it gets. This will indeed be a highlight of your Cape Cod adventure.
Elwood’s Raw Bars- Voted “Best of Cape Cod” Raw Bar award in 2025 A true raw bar experience, with Chatham oysters shucked right in front of you, plus fun grilled oyster variations (lemon-parm, bourbon-chipotle, etc.). They’re all to die for!
Viera on Main- A standout dining destination nestled in the heart of downtown Chatham, known for its locally inspired coastal cuisine and Cape Cod roots.
Chatham Fish Pier Market – Casual, but iconic. Grab a lobster roll or fried clams and watch the daily catch being unloaded from fishing boats—it’s a true Cape Cod experience. Famous for seafood right off the boats; oysters, lobsters and clams don’t get fresher than here. You can even watch the fishermen unload their catch while you eat and seals will poke out to say hi!
Beach House Grill- Tucked into the sand dunes of Chatham Harbor, the Beach House Grill is the ultimate barefoot escape. Sip a glass of wine or a craft cocktail with your toes in the sand while savoring fresh-caught seafood in true Cape Cod style. It’s casual, coastal, and effortlessly chic.
The Impudent Oyster- A waterfront go-to known for vibrant ambiance. A cozy, slightly upscale restaurant with creative seafood dishes, including some of the best local oysters served chilled or dressed up.
Later, you might find yourself at Chatham Squire. Sip classic cocktails, chat with locals, and dance the evening away—it’s the perfect spot for a fun night out on the Cape.
Coffee Shops:
Snowy Owl Coffee Roasters
Coastal rustic meets Main Street charm at Snowy Owl. Tucked into a cozy, tree-shaded nook, this café feels like a hidden hideaway in the heart of Chatham. Inside, warm wood accents and twinkling string lights create the perfect cozy vibe with amazing lattes.
The Sill at Wequassett Resort
Nestled inside the dreamy Wequassett Resort, The Sill is effortlessly elegant with waterfront views that make every cappuccino taste like luxury. This is where you come in a crisp white linen dress, order a latte, and walk over to the harbor and watch it sparkle with every sip.
Three Fins Coffee Roasters
A sunken café made from an old pool! Three Fins Coffee Roasters transformed the former swim club’s pool into a brand-new café and cacao factory. The vibe is extra cozy, with bean bag chairs tucked into the “deep end” and vintage surf films playing on loop, giving it a laid-back, coastal feel. All of their pastries are amazing and the lattes are expertly crafted.
Chatham Perk
This spot feels like a locals favorite! There’s always a line that makes you feel like you’re “in the know” and anything you order will be tasty. My favorite being the breakfast sandwiches on Portuguese muffins.
Chatham blends laid-back Cape Cod nostalgia with an elevated chicness. Whether you’re here for shopping, sailing, or the seafood Chatham is the kind of place that makes every summer day feel like it belongs in a storybook!
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