From its tranquil accommodations and contemporary art spaces to quintessential summer pastimes and fine dining, Orleans offers an upscale yet relaxed atmosphere for discerning travelers. Whether you’re seeking natural beauty, cultural enrichment, or gourmet experiences, this town promises a perfect day of exploration and indulgence. Here’s a step-by-step guide to creating your ultimate Orleans itinerary.
Begin your day with serene water views and the cozy hospitality of A Little Inn on Pleasant Bay. This charming bed-and-breakfast offers a delightful start with homemade bread, a relaxing garden setting, and impeccable service. As you sip your morning coffee, keep an eye out for Eloise, the inn’s newspaper-retrieving dog, who adds an extra touch of warmth to your stay.
After breakfast, immerse yourself in cutting-edge contemporary art at READYMADE Gallery. As a satellite of New York City’s Freight + Volume Gallery, this space showcases innovative works from emerging and established artists, often tied to Provincetown’s DNA Artist Residency. The seasonal exhibitions, running May through November, offer a thought-provoking experience for art enthusiasts looking to engage with experimental and boundary-pushing pieces.
Nothing says summer on Cape Cod like an evening at Eldredge Park, cheering on the Orleans Firebirds. Part of the prestigious Cape Cod Baseball League, the games provide an authentic slice of Americana with a touch of coastal charm. Gather with locals and visitors alike to watch top collegiate talent play in this storied league during the June to August season.
As the day winds down, head to Rock Harbor for one of Cape Cod’s most stunning sunset experiences. At low tide, expansive sand flats emerge, perfect for an evening stroll or quiet reflection. With its calm waters and vibrant skies, Rock Harbor provides a picturesque backdrop for capturing the beauty of Orleans at dusk.
End your day on a high note at The Barley Neck, where refined tavern dining meets cozy Cape Cod ambiance. Known for its expertly crafted dishes featuring locally sourced ingredients, this restaurant is a favorite for its lobster risotto and warm hospitality. Whether you’re celebrating a special occasion or seeking a relaxed yet elegant meal, The Barley Neck delivers a memorable dining experience.
Orleans strikes the perfect balance between refined luxury and Cape Cod’s laid-back charm, making it an ideal destination for upscale travelers. From morning to night, the town offers enriching experiences and timeless coastal beauty. For those seeking a sophisticated escape on the Cape, Orleans is the perfect five-star destination.
This terrifically charming and well decorated bed and breakfast sits on the scenic shores of Pleasant Bay, offering stunning views of the water and lush gardens. Your stay comes complete with it's own mascot, the lovely newspaper retrieving Eloise. With nine uniquely decorated rooms, we personally rave about the cozy, New England-inspired décor and peaceful atmosphere. Many appreciate the homemade bread and wonder who could possibly manage to do such impeccable work day in and day out. The inn is well and rightly praised for its warm hospitality, with guests particularly enjoying the personalized service from the innkeepers. It’s an ideal spot for those seeking a quiet, relaxing retreat near Orleans and Chatham, open seasonally from May to October. Be on the lookout for wine hour, every evening.
READYMADE Gallery is a dynamic space opened in 2023 as a satellite location for New York City’s Freight + Volume Gallery. The gallery features a rotating program of group exhibitions that focus on contemporary and experimental art. Many of the featured artists are participants of the DNA Artist Residency, located in Provincetown, which fosters creative output by offering studio spaces to emerging artists. READYMADE’s exhibits are eclectic, challenging traditional forms and themes, making it an exciting visit for those interested in cutting-edge contemporary work. It operates seasonally, from May through November.
Rock Harbor is a picturesque beach and harbor, well-known for its vibrant sunsets and tranquil atmosphere. At low tide, the beach offers vast sand flats, which are perfect for walking, exploring tidal pools, and enjoying the scenery. The harbor is also a popular launching point for fishing charters. There is no fee for parking, and no permits are required, but beach fires are prohibited.
This upscale tavern-style restaurant offers a cozy, rustic dining experience with an emphasis on locally sourced ingredients. The lobster risotto is a standout dish, often mentioned for its creamy texture and fresh lobster. The Barley Neck is open year-round and is known for its intimate setting and excellent service, making it a great spot for both casual meals and special occasions.
Subscribe to get HyperLocal updates delivered directly to your inbox each week. Our newsletter is the best way to stay connected to what's new on the Outer Cape year-round!
