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Five Star Day: Chatham

Chatham, Massachusetts, epitomizes the refined charm of Cape Cod, offering a perfect blend of historic landmarks, serene coastal beauty, and world-class dining.
Boats sitting in Chatham Harbor on a calm, cloudy day.

With its picturesque streets and vibrant cultural scene, this seaside town is a haven for discerning travelers seeking an elegant yet relaxed experience. From indulgent breakfasts to romantic dinners, Chatham invites you to savor life’s finer pleasures. Here’s a curated itinerary for your ultimate five-star day in Chatham.

Breakfast at The Chatham Filling Station

Start your day with a hearty breakfast at The Chatham Filling Station, a cozy diner loved for its welcoming ambiance and delicious comfort food. Don’t miss their signature corned beef hash, prepared with fresh ingredients and bursting with flavor. Open year-round, this spot offers the perfect combination of local charm and culinary satisfaction, setting the tone for a delightful day ahead.

Late Morning Swim at Forest Beach

Once you've had a chance to digest breakfast, head to Forest Beach for a peaceful escape by the sea. This hidden gem in South Chatham boasts calm, shallow waters ideal for a refreshing swim or a leisurely stroll along the shoreline. Surrounded by marshlands, the beach offers excellent birdwatching and tranquil views of distant boats. Its uncrowded atmosphere ensures a serene retreat, even in peak summer.

Gift Shopping at Gustare Gourmet

Indulge your culinary senses with a visit to Gustare Gourmet, a specialty shop renowned for its premium olive oils, vinegars, and artisanal ingredients. Perfect for the food enthusiast, the store offers an array of flavors to elevate your cooking and make thoughtful gifts for loved ones. Open year-round, Gustare Gourmet provides an elegant shopping experience in the heart of Chatham.

Take a Tour at the Chatham Lighthouse

Discover Chatham’s maritime heritage with a tour of the iconic Chatham Lighthouse. A symbol of the town’s nautical history, this working lighthouse offers breathtaking views of the Atlantic Ocean and Monomoy Island. Learn about shipwrecks, coastal rescues, and the lighthouse's role in guiding mariners since 1808. Tours are available during the summer, making it a must-see for history buffs and ocean lovers alike.

Romantic Dinner at The Chatham Cut

Cap off your day with an elegant dinner at The Chatham Cut, an upscale steakhouse with Mediterranean and Italian influences. Enjoy premium steaks, fresh seafood, and an impressive wine library in a sophisticated yet welcoming setting. For a truly indulgent experience, try the bone-in veal chop Milanese, a standout dish that pairs beautifully with a curated glass of wine. Open year-round, The Chatham Cut is the perfect place for an unforgettable evening.

Chatham blends timeless coastal elegance with modern sophistication, offering upscale travelers an exceptional Cape Cod experience. From tranquil beaches to exquisite dining, the town promises an enriching day filled with beauty, culture, and indulgence. Plan your visit to Chatham and discover the magic of this quintessential New England destination.

A picturesque stack of three blueberry pancakes on a white plate seated on a line-art table cloth. The pancakes are topped with powdered sugar. There's a place setting to the right of the plate and the sun comes in from the right through an unseen window.

Chatham Filling Station

A local favorite for breakfast and lunch, The Chatham Filling Station serves classic diner fare with a coastal twist. Known for its warm atmosphere, this casual spot features items like fluffy pancakes and lobster rolls. One standout menu item is their corned beef hash, often praised for its fresh ingredients. Open year-round, it’s a great spot for a hearty, comforting meal any time of the year​.

An empty beach close to sunset. The water is very calm on the right, the sandy beach is on the left. Farther down the shoreline a treeline can be seen behind which the sun is going down.

Forest Beach

A quiet, lesser-known beach located in South Chatham, ideal for those seeking a more serene and private coastal experience. The beach is bordered by marshlands, offering opportunities for birdwatching, and the calm, shallow waters make it family-friendly. It's a great spot for leisurely walks and watching boats in the distance. Parking is limited but free, and the beach typically remains uncrowded, even in peak summer months. There are no facilities or lifeguards, dogs are only allowed in the off-season, and beach fires are not permitted, adding to its peaceful, natural vibe​.

The front of a painted white wooden shingled store that sells oils and vinegars. There is a door with many panes of glass to enter. It's daytime and very nice outside, there are flowers by the door. The sky is clear and blue.

Gustare Gourmet

A specialty shop focused on premium olive oils, vinegars, and gourmet ingredients, Gustare Gourmet is known for its curated selection of high-quality culinary products. While it’s not a full grocery store, it’s a great spot for food enthusiasts looking for artisanal ingredients to enhance their cooking. Open year-round, this shop is a destination for those seeking to elevate their kitchen game with Mediterranean flavors.

A couple of slices of slightly overcooked steak on a bed of vegetables with yellow tomatoes. Beyond the plate is a full water glass, a full champagne flute, some cocktails, and other dishes on the table to enjoy.

The Chatham Cut

The Chatham Cut is an upscale steakhouse with a Mediterranean and Italian influence, combining sophisticated flavors with a welcoming atmosphere. It features a hand-selected wine library with over 320 bottles and offers premium steaks sourced from Boston’s top butcher. Seafood lovers can also enjoy dishes like bouillabaisse and sea scallops. A standout dish is the bone-in veal chop Milanese. The restaurant is open year-round, though hours may vary during the off-season​.

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