The Cape is calling, and we’ve got you covered with an expert guide to this idyllic town. 
Where To Eat
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359 Main St., Suite 2/ cuveechatham.com
Situated inside Chatham Inn, Cuvée offers an elegant dining experience with the freshest fish and delectable desserts. The four-course chef’s menu, curated by executive chef Isaac Olivo and pastry chef Whitney Stancil, features dishes like striped sea bass with Jerusalem couscous, while the seven-course tasting menu serves up bites such as day boat sea scallops served with grapefruit and fennel.
524 Main St./ chathamcookware.com
Looking to pick up provisions for your next beach picnic? Chatham Cookware is a local favorite for tasty grilled paninis, baked goods, mouthwatering sandwiches, soups and more. After grabbing a cinnamon twist and cup of joe by Beanstock Coffee Roaster’s for the road, order the Sandpiper panini with honey ham, triple cream brie, granny smith apples, caramelized onions and honey mustard.
907 Main St./ delmarbistro.com
Native seafood and wood-fired, thin-crust pizza meet an ideal nightlife scene at this Chatham favorite. Enjoy dishes like pan-roasted halibut with charred scallion and miso lobster butter while admiring the artwork of local artist Odin K Smith's artwork, which lines the eatery's walls.
2173 Head of the Bay Road/ wequassett.com
Treat yourself to an evening at the renowned Twenty-Eight Atlantic, where a three-course prix fixe and seven-course tasting menus wow. Visitors can indulge in heavenly delights like butter-poached lobster tail, oysters with caviar and tuna while taking in the historic ambiance of the 18th-century sea captain’s home.
Where to Stay
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297 Shore Road/ chathambarsinn.com
Built in 1914, Chatham Bars Inn combines stunning oceanfront views with unbeatable hospitality. Once guests check in, they can explore six on-site restaurants boasting local seafood, farm-to-table fare, signature cocktails, and stunning vistas. The property also offers a quarter mile of private beach and convenient proximity to the town’s bustling Main Street.
359 Main St./ chathaminn.com
Although Chatham Inn, Relais & Châteaux is the oldest hotel in the area, the property features an abundance of modern luxuries for travelers to enjoy. Eighteen recently renovated guest rooms and suites exude the timeless charm of the 1830s while rotating showcases of art by locals like Steve Lyons and Paul Blackmore adorn the hotel’s walls.
Where to Relax
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297 Shore Road/ chathambarsinn.com
Unwind and recharge at The Spa at Chatham Bars Inn, where five dedicated treatment rooms and a range of rejuvenating treatments await. Before treating yourself to sea salt scrub or vitamin C facial, find pure serenity in the Zen Room, relax in the dry sauna or take a dip in the heated pool.
35 Cross St./ thelepetitedayspa.com
Escape the hustle and bustle of your Cape Cod summer with a visit to Le Petite Day Spa. Owned by Chatham local Kim Carlin, this idyllic retreat offers a variety of treatments to help you relax your mind, body and soul, including massage and hot stone therapy, skin treatments and more. For those seeking a comprehensive experience, Le Petite Day Spa also offers spa packages complete with facials and aromatherapy.
Where To Shop
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492 Main St./ chathamart.com
Chatham Fine Art is a must-visit destination for art enthusiasts seeking a memento from Cape Cod. Explore an extensive collection of paintings and prints from approximately 50 artists. With over 600 displayed paintings, you will surely find the perfect piece for your taste. If not, the knowledgeable staff at Chatham Fine Art will assist you in locating the ideal artwork.
400 Main St./ thehouseoffindings.com
Whether you’re looking for the perfect summer party dress or to refresh your summer wardrobe, House of Findings has you covered. The chic shop, founded by creative director Mayra Gonzalez, specializes in sustainable fashion, vintage pieces and handmade apparel—all to help you achieve that elevated, one-of-a-kind look.
595 Main St./ portsandcompany.com
For two decades, Ports and Company has been a go-to boutique for all things stylish in Chatham—think statement hats, heels, flowy summer dresses and more. Bright pops of color and elegant designs from brands like Pearl & Caviar, Pranella and Margaret O’Leary are sure to catch your eye.
For Pre-Dinner Drinks
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593 Main St./ vieraonmain.com
Whether you’re in the mood for a Chatham-inspired Main Street Mai Thai or a refreshing cucumber and fresh-mint Yoga Mommy, this downtown favorite satisfies every palate. Kick off your evening with their salted caramel martini, featuring a salty pretzel-rimmed glass for a unique twist.
512 Main St./ wildgoosetavern.com
Dubbed “The Goose” by locals, Wild Goose Tavern is a downtown gem you don’t want to miss. Enjoy the lively atmosphere while sipping one of their playful takes on classic cocktails, including four versions of an old-fashioned. Our favorites are the coconut cocoa rum old-fashioned with demerara syrup and the tequila old-fashioned with bourbon maple syrup.
Where To Hit The Town
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637 Main St./ chathamorpheum.org
Spend your next rainy evening at Chatham’s first movie theater. Now boasting a modern, first-class cinema, the historic theater offers a diverse selection of movies, from major motion pictures to classic films, independent productions and even the works of local filmmakers. Whether you’re in the mood for new releases like The Little Mermaid or a thrilling classic like Jaws, there’s something for everyone.
Cultural Experiences
37 Main St./ historic-chatham.org
As one of the only lighthouses in the United States to still operate 24 hours a day, Chatham Lighthouse is a historical treasure and a must-see attraction. Known as the “Twin Lights” to locals, this impressive 48-foot edifice flashes twice every 10 seconds, guiding ships safely to the harbor. Visitors can learn about the rich history of the lighthouse during a beach walk at Chatham Lighthouse Beach.
30 Wikis Way/ fws.gov
In Southern New England, Monomoy Wilderness is only one federally designated wilderness area. Spend an afternoon connecting with nature at the trailblazing wildlife refuge, where serene hiking trails along Morris Island Trail and rare sightings of Monomoy’s migratory birds, gray seals and other wildlife abound.
Hidden Gem
435 Cockle Cove Beach Road/ chatham-ma.gov
For an authentic feel of Chatham’s iconic seaside origins, head to Cockle Cove Beach. The calm, warm waters of the Nantucket Sound make the spot ideal for swimming, windsurfing and kayaking.
Photography by: Courtesy of Chatham Inn, Relais & Châteaux
