A local favorite, The Chatham Squire offers a cozy, casual atmosphere with fresh seafood and pub fare. Enjoy a cold drink on the patio, or relax inside by the fire while savoring their renowned clam chowder. It’s the perfect spot for a laid-back meal with a touch of New England charm.

For a delicious seafood experience, head to Mac’s Seafood and try their mouthwatering blackened tuna sandwich. This casual seafood market and eatery is known for its fresh, high-quality dishes and relaxed vibe. Whether you're grabbing lunch or dinner, it's a must-visit for seafood lovers.

A nostalgic childhood favorite, Buffy’s is filled with playful charm, including the Calvin and Hobbes mural on the wall. Grace recommends the hot pink sprinkles, while Mike swears by the coffee oreo ice cream. With its colorful treats and whimsical atmosphere, it’s the perfect spot to satisfy your sweet tooth.

A charming breakfast and lunch spot, Chatham Cookware is known for its delicious pastries and cozy atmosphere. It’s the perfect place to enjoy a cup of their amazing hazelnut coffee while indulging in freshly baked goods. Located right on Main Street (not far from the Squire our our church venue), it’s the perfect post-run pick-me-up.

Pate’s is the go-to spot for fresh, flavorful seafood, and their tuna cones are an absolute must-try. This family-owned market and eatery has been serving up some of the best seafood in Chatham for years. Whether you’re looking to dine in or take home a meal, Pate’s is a local favorite for fresh catches and creative dishes.

A quintessential Chatham experience, the Chatham Fish Pier Market offers fresh seafood right off the boats. Watch the fishermen unload their daily catch and select from an array of fresh fish, shellfish, and more. It’s a fantastic spot for grabbing seafood to cook at home or enjoying a casual, freshly prepared meal.

A stunning and historic destination, Chatham Bars Inn offers a variety of dining options across its many restaurants, perfect for a memorable dinner. If you’re looking to unwind, head to the veranda for a classic old fashioned while enjoying beautiful views of the ocean. Whether you’re dining or sipping a cocktail, it’s a must-visit for a taste of luxury and charm.

A hidden gem in Chatham, the Atwood Museum offers a fascinating glimpse into the town’s rich history and maritime heritage. Explore exhibits that highlight the area's early settlers, whaling history, and local culture. It’s a perfect spot for history lovers and anyone looking to dive deeper into Chatham’s past.

Founded in 1955, Chatham Candy Manor is a beloved family-run business known for its delicious, handmade sweets. Whether you’re craving chocolate, caramel, their famous fudge or classic saltwater taffy, this sweet shop is a must-visit for any candy lover.

A quirky and captivating shop, Maps of Antiquity specializes in rare, vintage maps and nautical charts. Whether you're a collector or just appreciate unique decor, you'll find something special among their beautifully framed pieces. It’s a whimsical stop where history and art coincide.

A true treasure for art lovers, Chatham Fine Art Gallery showcases a stunning collection of works from both local and national artists. With its diverse range of paintings, sculptures, and photography, the gallery offers something for every taste. It’s the perfect spot to discover new pieces and immerse yourself in the creative spirit of Chatham.

Coast Guard Beach, part of the Cape Cod National Seashore, offers a blend of natural beauty and rich history. Visitors can walk the historic Nauset Trail, which follows the same path the Pilgrims likely took when they first arrived in America, leading to a spectacular view of the beach. The beach itself is perfect for a scenic day of sunbathing, swimming, or simply enjoying the stunning cliffs and surf, with the Pilgrim Monument in Provincetown visible from certain vantage points.

A quaint gem in Chatham, the Eldridge Library is a must-visit for book lovers and history enthusiasts alike. Built in 1912, the library is housed in a charming, historic building with a cozy interior and a wide selection of books. It’s a peaceful spot to read, attend community events, or explore local history through their collections and exhibits. Pro-tip: visit the used book sale in the basement.

A quintessential Chatham experience, the Chatham Fish Pier Market offers fresh seafood right off the boats (go early in the morning!). Watch the fishermen unload their daily catch and select from an array of fresh fish, shellfish, and more. It’s a fantastic spot for grabbing seafood to cook at home or enjoying a casual, freshly prepared meal.

A Chatham classic, Marion's Pie Shop has been delighting visitors with its homemade pies since 1949. Known for its flaky, buttery crusts and delicious fillings, the shop offers a variety of pies, including fruit, cream, and their famous lemon meringue. Whether you're grabbing a slice to enjoy on the go or taking a whole pie to share, it’s the perfect place to satisfy your sweet tooth. Pro tip: they do soup and lasagna, too!

Located in Hyannis, the John F. Kennedy Museum offers a deep dive into the life and legacy of the 35th president. The museum showcases a range of exhibits, from personal artifacts and photographs to historical displays about JFK’s time in office and his connection to Cape Cod. It’s a must-visit for anyone interested in American history and the Kennedys’ lasting impact on the nation.

A charming coastal town located on Cape Cod, Wellfleet is known for its scenic beauty, art galleries, and delicious seafood. Famous for its pristine beaches, such as Marconi Beach and Wellfleet Bay Wildlife Sanctuary, it’s a perfect destination for outdoor activities like hiking, kayaking, and birdwatching. With its quaint town center, local shops, and renowned Wellfleet oysters, the town offers a peaceful yet vibrant atmosphere for visitors to explore.