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Just 90 miles from Boston, Massachusetts, the town of Orleans represents a quintessentially New England crossroads. It's where the peninsula's main arteries intersect, in the crook of Cape Cod's arm. It also serves as the bustling commercial hub for much of the Outer Cape. And it marries contemporary vibrancy with breathtaking natural splendor.
Exhibit A is its downtown area, which brims with New England charm and occasional eccentricity -- including its renowned Artist Cottages. For exhibits B through Z, look no further than its stunning beaches, lush forests, meandering hiking trails, and scenic bike paths, and an abundance of picturesque ponds, bogs, and inlets.
In this post, we’ll cover sights, activities, and tips to help you get the most out of your visit to this spectacular town, whether you’re simply day-tripping or settling here for an extended Cape escape at one of Del Mar Vacations' Orleans vacation rentals.
Top Sights in Orleans
The town of Orleans offers more than its share of must-visit attractions and sights, considering that simply exploring its beautiful coastlines is an extraordinarily rich and rewarding experience.
Take, for instance, the iconic tidal pools of the Skaket Beach, facing the calm Cape Cod Bay, and which go out nearly a mile at low tide. Facing the Atlantic Ocean is Nauset Beach, one of the gems of the Cape Cod National Seashore and a must-see destination in its own right. The fact is, with 10 miles of unspoiled coastline, this is where you’ll experience one of the most enchanting beach strolls anywhere.
Inland, popular attractions include Orlean’s beautiful Church of the Transfiguration, situated on the scenic Rock Harbor and noteworthy for its architectural representation of a 4th century style of Christian basilica.
Another notable historical attraction is the Jonathan Young Windmill, one of the oldest windmills in the US, and said to date back to 1720.
Orleans is also an exceptional entry point to the Cape Cod Rail Trail, with the Orleans-to-Harwich leg offering up some of the most scenic variety on the trail.
Best Activities You Should Do in Orleans
It really is no surprise that Orleans ranked on a Coastal Living list of “Happiest Seaside Towns in America”: blessed with exceptional shorelines, it’s also a hub for a host of engaging activities that cater to a wide range of interests.
Along with cycling on the Cape Cod Rail Trail, other highly popular activities include fishing charters, sunset kayak tours, paddleboard outings, and surfing.
Orleans also offers a wealth of opportunities for cultural and creative explorations, including the famous Artist Cottages on the Orleans Market Square, featuring pottery, photography, painting, and much more.
Tree's Place Gallery and the Addison Art Gallery offer further encounters with new talent as well as well-known artists, and the Academy of Performing Arts is also worth visiting for its year-round theater performances and musicals.
For retail activities, the downtown area is a hotspot for souvenir shopping, great food, and a very walkable Main Street.
Family-Friendly Activities
The welcoming, family-friendly nature of Orleans makes it an ideal destination for visitors of all ages, whether for leisurely beach days capering among Skaket Beach’s gentle waves to educational visits to the French Cable Station Museum, a historic telegraph station built in 1891.
Other outdoor adventures that are perfect for families include hiking in conservation areas such as Baker’s Pond or John Kenrick Woods, exploring the area around Pilgrim Lake, or picnicking at Eldredge Park, home field of the Orleans Firebirds baseball club.
In season, Cape Escape Orleans Mini Golf offers one of the most popular mini golf courses on the Cape, and the Orleans Bowling Center offers both bowling activities and smoked BBQ specialties with kids’ menus.
Activities If You Have Pets
With more and more visitors to Cape Cod traveling with pets, Orleans is gaining a reputation as a pet-friendly destination.
There are currently no dog parks in Orleans, but off-season, dogs are allowed on Nauset Beach, Skaket Beach, and Rock Harbor Beach.
Year round, dogs are permitted on the Cape Cod Rail Trail, as well as on hiking trails in the Kent’s Point and Paw Wah Pond conservation areas.
As far as dining options are concerned, dog-friendly restaurants include The Knack (seafood and burgers), The Block and Tackle (BBQ), Laurino’s Tavern (Italian and Mexican), and Chatham Sunrise (brunch and breakfast).
Explore pet-friendly rental properties
Where to Eat in Orleans
Orleans features a wide selection of highly recommended restaurants, cafes, and eateries, variously standing out for signature dishes, ambiance, and scenic views.
Here are just a few:
Land Ho!: A pub-style restaurant with a nautical theme, Land Ho! serves up hearty portions of comfort food favorites like clam chowder, fish and chips, burgers, and clam chowder. The friendly atmosphere and beer selection make it a popular spot for locals and visitors alike.
The Yardarm: With panoramic views of Town Cove (a popular spot for bird watching), The Yardarm provides a picturesque setting for fresh seafood and American classics. High praise goes to their burgers, fish and chips, and fried oysters.
Hole In One: For breakfast and brunch options, locals recommend Hole In One. This cozy diner-style eatery serves up breakfast platters, omelets, and fresh-baked donuts, pastries, and cupcakes.
Nauset Fish and Lobster Pool: A local favorite known for its classic New England seafood dishes, The Lobster Claw serves up fresh lobster, clams, scallops, and more in a cozy, family-friendly atmosphere.
Rock Harbor Grill: Serving wood-fired pizzas as well as new American classics, Rock Harbor Grill is a family-friendly tavern that features outdoor seating and great kids’ menu options.
Hot Chocolate Sparrow: Called the best ice cream shop in Orleans by some locals, Hot Chocolate Sparrow serves coffee, desserts, ice cream, and sandwiches to rave reviews.
Be sure to make reservations at popular spots, particularly if you’re looking to catch sunset views during dinner.
Orleans Travel Tips
Orleans offers stunning beauty and visitor attractions year-round, but as with all Cape Cod destinations, summertime is peak season, so this is when you’ll need to plan, book, and reserve well ahead of time, starting with vacation rental accommodations.
Del Mar Vacation Rentals is a favorite in the Cape Cod region, and offers a rich catalog of Orleans vacation rentals, including bay views, beach access, and intimate retreats.
Orleans is a great launch pad from which to visit other popular Cape Cod destinations, including Provincetown, Brewster, Dennis, Wellfleet, Eastham, Hyannis, and of course Martha’s Vineyard and Nantucket by ferry.
If you’re going this route, it’s highly advisable to drive in or rent a car, although there are numerous bus, taxi, and car hire services available. In season, travelers from Boston (Mass) can take the scenic route to Cape Cod aboard the Cape Cod Regional Transit Authority’s passenger train.
What Locals Love About Orleans
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About the Author
In 2015, driven by his own challenges as a homeowner dealing with a rental management company and a desire for a better solution, Luke Chapman founded Del Mar Vacations. His goal was to simplify the process of managing and caring for rental homes and their guests, offering a comprehensive, full-service solution. As a lifelong Cape Codder, Luke's deep-rooted love and knowledge of the area infuse every aspect of his business. Through this blog, he shares his insider tips and local insights, aiming to transform each visitor's trip into an unforgettable Cape Cod adventure.