Your Cape Cod vacation in Orleans is going to be one filled with beautiful beaches, scenic views, delicious seafood, and because you chose Pretty Picky Properties for your vacation accommodations, one that is more comfortable than any you have experienced before. If you’re looking for a place that offers relaxation, visit Orleans and discover why it’s one of Cape Cod’s best-kept secrets. The town of Orleans isn’t as well-known as some of the other towns and villages on the Cape, so today we want to give our guests a tour of everything that makes this town special, homing in on some of the top sights and attractions and leading the way back home to our Orleans retreat at day’s end.
This ultimate guide to Orleans may not make your decision of where to stay any easier, but it will give you a deeper understanding of Cape Cod and all the wonderful things you have to look forward to when you finally land on our sandy shores.
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Welcome to the South Parish of Eastham!
We can see the question mark in your eyes from here as you curl your brow and think to yourself, “I thought we were exploring Orleans?” So, no, we haven’t pulled the rug out from under you, we are just referring to Orleans original name, given to it many centuries ago. Settled in 1644 and incorporated in 1797, at which time the South Parish of Eastham was given the name of Orleans, throughout the years, the sea—more precisely, the fishing industry—was the chief source of employment and income for those that lived here, and until the Cape Cod Canal was built, this area experienced a plethora of shipwrecks.
Today, Orleans is remembered for being the only US site to have been attacked by Germans during WWII, when a German U-boat fired upon the tug Perth Amboy and four barges in the Nauset area, but that wasn’t its first brush with wartime issues. During the war of 1812, Rock Harbor was the site of a British attack, as the Brits fought to get America back under rule of the crown, obviously failing in the overall attempt, as well as failing to overtake Orleans, thanks to the dedicated response from our local militia.
It’s Always a Good Day at the Beach
Orleans is a beautiful town, and we know you will fall in love with it, probably within seconds of arriving, but we also know what drew you to our sandy shores and that would be those sandy shores themselves. A day at the beach on Cape Cod has been an all-American dream almost since travel was made simpler with the Cape Cod Railway, and your dreams are about to come true with a visit to Nauset Beach.
Offering 10 miles of coastline, the warmer waters make it an ideal spot for swimmers, surfers, and body boarders, and on some sections of the beach, Over Sand Vehicles (OSV) are allowed with the proper permit. Lifeguards are on duty from June through September, making moms from all over the world feel safer about their kids’ swimming adventures, and starting on the first Monday in July, the Nauset Beach Concert Series adds free music to your beachy adventures, with local musicians performing rock, blues, jazz, and so many other music genres at the Nauset Beach Gazebo. This is a popular beach, so plan on arriving early in order to get a prime spot and if you bring a cooler filled with food and beverages you don’t have to leave until after the sun sets; Nauset Beach is also a prime sunset watching location!
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Top Attractions and Things to Do in Orleans
As we mentioned earlier, Orleans isn’t as well-known as some of Cape Cods other towns, but we can assure you that there are some pretty cool attractions located within city limits, with our favorites listed below.
Jonathan Young Windmill, 41 Old Kings Highway
There are a few windmills you can see during your Massachusetts journey, but the Jonathan Young Windmill is unique in the fact that it still has all its original parts and machinery, something those other windmills can’t claim. Built in the early 18th century, it was moved from its original location in South Orleans to the Overlook on Town Cove in 1839 before moving to its current location after some relatively recent renovations. Sitting at water’s edge in a small park that offers stunning views, great fishing, and picnic tables, the windmill was once used to grind grain for settlers meals. Today, it serves as a reminder of those simpler times, providing a great selfie spot, and as you pose in front of the windmill, we’re sure you will get all the likes on your favorite social media sites!
French Cable Station Museum 41 S Orleans Road, Open Weekends 1PM-4PM
Back in the days before internet, people kept in touch through telegraph stations and the French Cable Station provided a direct connection to France, even going as far as to be known as “Le Direct.” Installed in 1891, the cable used for this purpose was over 3000 miles long, if you can imagine, and the station stayed in use until 1952, except for a few years during WWII when it was shut down for security purposes. Remember, Orleans was the site of the only attack by Germans during that war, and so it wouldn’t have been a stretch to imagine that the cable could have been used with ulterior motives during wartime. Today, it serves as a reminder of those simpler times, offering a variety of artifacts that are displayed throughout the museum, with some of the equipment found inside actually still being operational.
Addison Art Gallery, 43 S Orleans Road
Some of the world’s most talented artists make their homes in Orleans, and the Addison Art Gallery displays the best of their creations, including wood sculptures, paintings, and photography with most of the subject matter being life on Cape Cod. This display of art never fails to amaze us and presents the most unique of Orleans souvenirs; just one painting of a silent canoe sitting at shore’s edge at sunset will forever remind you of the sunsets you fell in love with during your stay!
Celebrating Orleans
Have you ever visited someplace new and come across an art show, a carnival, even a founders day celebration? Being able to attend this surprise events makes you love the place you are visiting even more, feeling a part of their town and making you want to return again to see what other wonderful surprises are in store for you. When you visit Orleans during the dates listed below, you will get to experience that wonderful sense of belonging for yourself and the memories you will make will be even sweeter!
Cherry Blossom Festival/Market in the Park, Mother’s Day Weekend, Orleans Village Green
Spring has sprung by the time Mother’s Day Weekend rolls around, and after our long and snowy winter, we are more than ready to celebrate cherry blossoms, sunshine, and the really cool things being sold by local vendors! Offering live music and the opportunity to dance around the figurative May Pole (ok, there’s no May Pole, but there WILL be dancing), those traveling with children will be delighted to learn that there is a kids’ craft area with outdoor activities for them to enjoy as well and perhaps be even more delighted to explore the food trucks and refreshments supplied by Truro Vineyards and Hog Island Beer Company. (We know we sure were.) This event is a free one, but don’t leave your wallet behind; you’ve got a lot of shopping to do, and that wine, beer, and food isn’t free!
Nauset Summer Crafts Festival, August, Nauset Regional Middle School, 70 MA-28
We envy the talents of local arts and artisans, wishing we shared in their skills, but since we don’t, we eagerly await the Nauset Summer Crafts Festival held every August at our Nauset Regional Middle School. This two-day event is known for offering 75 juried all-American handmade arts and crafts, as well as specialty food sampling booths where guests can enjoy a taste of homemade jams, sauces, candy, seasoning, even gourmet nut butters, with each sample convincing us that, yes, we need that product at home. Free demonstrations may encourage you to try your hand at crafting or jelly making, and free entry and parking ensure that you will have more money to spend on cool gifts and delicious treats!
Outermost Roots & Blues Festival, October, Nauset Beach
By October, most of Cape Cod has returned to its normal quiet and peaceful self, and although tourist season is over, Orleans find this month is the perfect month to celebrate music at the beach. The Outermost Roots & Blues Festival, held every October since 2018 (with the exception of a couple of COVID years), serves as a reminder that music and beach days should always go hand in hand, and as the music plays, the sea roars, and guests find themselves dancing in the sand, you too will be a fan of this exciting festival in Orleans, perhaps returning every year just to dance.
A Taste of Orleans
Now it is time to partake in everyone’s favorite part of vacation life, savoring a taste of Orleans at these amazing Cape Cod restaurants listed below. We’ve done the research, repeatedly on occasion, and we can assure you that these wonderful spots will be where your best meal memories are made!
Homeport Restaurant, 55 Main Street, Open Daily at 6AM
There’s an old bit of advice that tells us we should eat breakfast like a rich person would, lunch like a middle class person would, and dinner like we don’t have two cents to our names. Of course, this was meant as a way of making sure we don’t overeat, but it still leads us Homeport Restaurant for breakfasts that are hearty and delicious. A neighborhood staple for over 50 years, Homeport is also a favored lunch and dinner spot as they are open until 9PM every day except Tuesday, when they close at 2. Serving meals created with locally sourced ingredients, don’t ask us what our favorite meal is because every dish that we try is our favorite at the moment. We will say that the pancakes are fluffy, the omelets are laden with ingredients, and their benedicts are sensational!
Mahoney’s Atlantic Bar & Grill, 28 Main Street, Closed Sundays
You’re on Cape Cod, and when it is time to eat, you want to eat like you are on Cape Cod, and Mahoney’s Atlantic Bar & Grill is our first suggestion while in Orleans. Offering a New England menu that includes an authentic clam chowder and a pan roasted lobster that will make your taste buds cry with joy, whatever you order, be sure to save room for Baby Cake Gingerbread or our personal favorite, Molten Chocolate Cake! Their Chocolate Dessert Martini is pretty special as well, so sip away if you just can’t eat another bite.
The Beacon Room, 23 West Road, Closed Mondays & Tuesdays
Is your vacation to Cape Cod a celebration of an anniversary, a birthday, or some other special occasion? Or are you just in the mood to celebrate a Friday in paradise with a fantastic meal? Either way, the Beacon Room will provide a meal worth celebrating, serving a classic Italian seafood menu with class and skill. Offering a romantic patio under a tent so that the elements won’t intrude on your delicious meal, this fantastic restaurant is also known for its holiday meals that help take the burden off mom! We guess the downside to eating here is when you try their Faroe Island Salmon and you will never be satisfied with ordinary salmon again, but sometimes you just have to take the good with the bad.
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Find Happiness at Home with Pretty Picky Properties
All our Lower Cape vacation rentals are uniquely beautiful and wonderfully comfortable and the ones we offer in Orleans are sure to fit your family’s needs, like a fine leather glove. Offering properties with as few as 2 bedrooms or as many as 6, they also come equipped with an extensive list of amenities that can include swimming pools, hot tubs, water views, firepits, and so much more. Reserve your favorite Pretty Picky Properties Orleans retreat today and come home to comfort every night of your stay!
