Blake Walsh

20 Best Things to Do in Orleans, MA

  • Published 2023/02/03

Charming, scenic, and nostalgic—these are the words that come to mind when trying to identify what makes the small-town charm of Orleans exceptional.

The town is set along the spectacular beaches of the Atlantic Ocean, where you can enjoy the relaxing sight of the glistening blue waters.

Orleans is also an arts mecca for art enthusiasts and a hotspot for history buffs.

This small town along Cape Cod will surprise you with many exciting activities to keep your trip brimming with adventures.

If you’re planning a trip to this town in Massachusetts soon, read on for the 20 best things to do in Orleans!

See the Historic Jonathan Young Windmill

Exterior of Jonathan Young Windmill

Jon Bilous /

Do you adore the sight of historic structures while exploring the town?

Then check out the historic Jonathan Young Windmill in Orleans built in the early 1700s.

The preserved windmill features its restored original parts, including the intact machinery.

Front view of Jonathan Young Windmill

Jon Bilous /

This windmill sits in front of the charming scenery of the glistening blue waters in a beautifully landscaped park.

Pack some snacks and bring your favorite book because this charming destination in town is perfect for a relaxed picnicking and unbothered reading with beautiful scenery.

The Jonathan Young Windmill is a historical gem of Orleans where you can learn about the town’s heritage.

View of Jonathan Young Windmill's historical marker

m01229 from USA, CC BY 2.0, via Wikimedia Commons

Cast Your Lines to Reel in the Fresh Catch from the Pilgrim Lake

Escape the hustle and bustle of the town by going on a laid-back trip to Orleans’ largest freshwater pond, the Pilgrim Lake.

The Pilgrim Lake extends to 43 acres, where you can enjoy a plethora of recreational activities.

Cast your fishing lines, wait for the fish to grab your bait, and reel in for the fresh catch from the Pilgrim Lake.

Paddle as you explore the waters on a paddleboard or a kayak, where you can enjoy the relaxing sight of the glistening waters and lush greeneries.

Aside from paddling and fishing, you can also set up a picnic for the family to enjoy and wade the fresh waters of Pilgrim Lake.

Hike the Trails of Kent’s Point Conservation Area

If you’re looking for a relaxing outdoor adventure, head out for a hiking trip at Kent’s Point Conservation Area.

This location is a nature respite among the bustling town of Orleans, where you can enjoy the sights and sounds of nature.

A scenic hike through Kent’s Point trails will take you through the woody paths that lead out to a small beachfront.

This destination is perfect if you want a relaxing hike without the daunting task of going through difficult paths.

Don’t forget to pack your outdoor trip essentials and go on a calming nature trip at Kent’s Point Conservation Area.

Bask under the Sun at the Nauset Beach

Nauset Beach aerial view

Ethan Daniels /

A trip to Orleans wouldn’t be complete without spending a vibrant day at the Nauset Beach.

Nauset Beach is popular among tourists because of its soft, sandy beach that extends for 10 miles.

This beach in Orleans is the go-to destination if you enjoy going on beach trips.

Bask under the sun while you listen to the relaxing sound of the waves crashing the shore.

Nauset Beach sunrise

HeFou /

Don’t forget to witness the sun fading through the horizon as it sets and marvel at the golden hour by the beach.

Pack your beach trip essentials and head out for a relaxing day spent at the beach that will truly delight both the young and the young at heart.

Whether you’re looking for some thrilling water recreation activities or you want to relax under the beaming sunshine, Nauset Beach is the perfect destination for you!

Delve into Orlean’s Art Scene at the Addison Art Gallery

Explore the town’s art scene by checking out the fascinating art exhibits at the Addison Art Gallery.

This gallery in Orleans showcases the works of emerging and renowned artists from the United States, Mexico, and France.

Marvel on the wonderful imagery brought by the combination of fascinating colors, strokes, and techniques used in the eclectic collection of artworks on display.

This quaint art gallery in Orleans is truly a gem if you’re an art enthusiast looking for works that would inspire and resonate with you.

Aside from the unique art pieces, you can also join events organized at the museum, like art shows and more!

Appreciate Orlean’s Contemporary Arts at Tree’s Place

If you’re looking for another stop in Orleans where you can see more of the artistic community in town, stop by the Tree’s Place Gallery.

Tree’s Place is another quaint gallery in Orleans that features a collection of works from renowned and emerging artists in the region.

Founded in the 1980s, the Tree’s Place Gallery has been an abode for artists and art enthusiasts to celebrate the arts.

As you walk through the gallery, you’ll see an eclectic collection of contemporary artworks in realism, impressionism, and post-modernism forms.

Whether you’re an art enthusiast wanting to be inspired by the artwork or an art collector looking for works that would resonate with you, Tree’s Place is the ideal destination!

Take a Trip Back in Time at the French Cable Station Museum

Exterior of the French Cable Station Museum

James Kirkikis /

Have you ever wondered how communication systems were back in the days without smartphones and social media?

Then check out this quaint gallery in Orleans that showcases the history of communication before instant messaging and long-distance calling were invented.

Geek out on the fascinating communication equipment from the Trans-Atlantic communication during the early 1860s up to its closing in the 1950s.

Front View of French Cable Station Museum

John Phelan, CC BY 3.0, via Wikimedia Commons

Whether you’re a history buff, a tech enthusiast, or a curious person, plenty of remarkable displays in the museum will pique your interest.

You can also get a unique souvenir in the form of a Morse code message generated by the original equipment from the exhibits.

A visit to the French Cable Museum is perfect if you’re looking for something quirky and interesting to do on your trip to Orleans.

Stroll through Downtown Orleans to Shop and Dine

Complete your weekend getaway on a shopping spree in the downtown area of the town of Orleans.

The vibrant Main Street of Orleans makes for a shopping hotspot if you want to shop for unique items as a souvenir on your trip to Massachusetts.

A shopping spree usually needs the daunting task of long walks, but the shopping hubs in Downtown Orleans are conveniently walkable, which means you can scour through the shops easily.

After your stroll through the shops, check out the selection of restaurants and cafes for some rest and an energy boost.

Downtown Orleans makes for an idyllic shopping and dining experience without the hassle of going on long walks, so don’t forget to stop by and support the town’s local businesses.

Tee Off at Cape Escape Adventure Golf

If you enjoy swinging your golf club in a themed mini-golf course, then don’t miss out on a fantastic experience at Cape Escape Adventure Golf.

This 18-hole mini-golf course in Orleans is set on a nautical theme featuring authentic fish boats, a Koi fish pond, and beautiful waterfalls.

You can put through the quirky yet challenging golf courses that are relatively easy for all ages.

Beat the quirky, varied holes that will take you through caves, boats, ponds, and waterfalls to enjoy a fun mini-golf experience.

After your golfing game, you can ask for fish food when you turn in your clubs for a chance to feed the Koi fish.

The Cape Escape Adventure Golf makes for an idyllic family bonding experience filled with fun and games that will delight the young and the young at heart.

Learn about the Local History at the Orleans Historical Society

Exterior of Orleans Historical Society in Orleans

John Phelan, CC BY 3.0, via Wikimedia Commons

A trip to Orleans wouldn’t be complete without learning about the town’s local history.

Check out The Centers for Culture and History in Orleans to discover the town’s fascinating history dating back from its early settlers up to its modern development.

The museum is housed on a Greek Revival structure registered on the National Register of Historic Places.

The museum showcases a collection of artifacts, archives of genealogical information, and photographs of the town’s people.

Whether you’re a history buff or a curious person, a trip to The Centers for Culture and History in Orleans is a must.

Try the Nostalgic Candlepin Bowling at The Alley Bowling and BBQ

If you’re caught in bad weather on your weekend getaway in Orleans, it doesn’t mean that the fun must end!

Nothing beats the classic indoor family fun at The Alley Bowling and BBQ for uninterrupted fun, whatever the weather.

Try your bowling skills in the real 1950s style candlepin bowling where everything is made of wood for a unique nostalgic bowling experience.

After a round of bowling, make sure to try the famous BBQ combined with sides and cold beverages for an energy boost.

A bowling game to The Alley Bowling and BBQ makes for a unique, memorable experience to delight all ages!

Go on a Nature Trip at the Twinning’s Pond Conservation Area

Escape the hustle and bustle of the town and take a breather away from your daily cares on a nature trip to the Twinning’s Pond Conservation Area.

This nature reserve is nestled in the south of Orleans, boasting excellent water quality and lush greeneries for the thriving wildlife in the area.

Hike through the wonders of the woods along the pond, where you can enjoy the sight of the enchanting pond glistening under the sun.

Twinning’s Pond Conservation Area is the ideal location to get lost in nature and keep your worries away as the calming ambiance of the place embraces you.

Be sure to grab the opportunity for outdoor exploration in this nature respite among the suburbia of Orleans.

Book Your Stay at the Orleans Waterfront Inn

Exterior of Orleans Waterfront Inn

ToddC4176 at the English Wikipedia, CC BY-SA 3.0, via Wikimedia Commons

If you’re looking for a place to stay on your weekend getaway, you can never go wrong on the charming Orleans Waterfront Inn located along Old County Road.

This inn in Orleans boasts a rich historical background dating back from its establishment in 1875.

The Orleans Waterfront Inn offers all necessary amenities to ensure your comfortable stay, including breathtaking harbor views.

This cozy waterfront inn in Orleans is the perfect place to crash after your fun adventures in Cape Cod.

Enjoy the comforts of this charming inn, where you’ll feel at home without being too far away from tons of exploration opportunities.

Go Ice Skating at Charles Moore Arena

Ice skating is a quintessential activity to make memorable experiences with the family no matter the season.

So make sure to hit the rink of Charles Moore Arena open year-round for an enjoyable ice skating experience with everyone.

Whether you’re looking for a fun family past-time, bonding with friends, or an exciting date activity, you can never go wrong with hitting up the skating rink!

Aside from ice skating, you can also join public events organized by the Charles Moore Arena, like hockey games and more!

Remember that it’s not guaranteed you won’t fall in the rink, but you can always get back up to laugh it off and enjoy your ice skating experience at Charles Moore Arena.

Chill Out with the Best-Tasting Craft Beer from Hog Island Beer Co.

Chill out while chugging the best-tasting craft beer paired with hearty Hog Island Beer Co snacks.

The Hog Island Beer Co. is dedicated to serving exceptional quality beers and spirits.

Whether you’re looking for a crisp and clean beer, sweet and malty brew, or a dark and roasty flavor, this microbrewery got you covered!

Aside from the selection of craft beer flavors, you’ll surely enjoy the chill ambiance of the brewery.

The Hog Island Beer Co. is set on the Little Pleasant Bay that overlooks the beach so that you can enjoy your cold beer near the picturesque setting.

Don’t forget to stop by the Hog Island Beer Co. for some crisp cold beers matched with hearty eats to delight your taste buds on your trip to Orleans.

Explore the Academy of Performing Arts

Academy of Performing Arts is a cutting-edge theater space that offers the Cape Cod community opportunities for interactive learning, art, and enjoyment.

The Academy has been imparting performing arts instruction to students of all ages since its founding in 1975.

They are dedicated to giving as many chances for all students and performers to perform.

Students desiring to advance their abilities in theater, song, dance, and as many design components as they can are the Academy of Performing ArtsArts’ core mission.

They provide theater and courses for everyone to embrace the community surrounding them.

Escape Stress and Head to Skaket Beach Motel

A pleasant accommodation in a convenient setting, the family-run Skaket Beach Motel is located in Orleans, Massachusetts.

They provide facilities for relaxation and enjoyment around the site and outside of your accommodation, including an outdoor seasonal pool, picnic spots, and grills.

A family apartment, multiple-room suites, wide guest rooms, and on-site laundry facilities are available.

Each room at the Skaket Beach Motel has a flat-screen cable TV, a fridge, microwave, coffee machine, blow dryer, iron, and ironing board.

The Skaket Beach Motel provides lots of space to relax throughout your vacation.

Drink and Dine at Mahoney’s Bar & Grill

Mahoney’s Bar & Grill is situated in downtown Orleans, a chic and upmarket dining establishment with a bustling bar and a welcoming dining room.

The restaurant’s setting, a 19th-century structure that once housed a dry good and penny candy shop, radiates warmth and style.

Mahoney’sBar & Grill delivers upscale New England cuisine in a welcoming, informal setting with all the flair of a Boston club.

Chef Ted Mahoney has created a comprehensive, diversified cuisine focused on fresh, local seafood to satisfy customers’ interests.

Enjoy top-notch cuisine in the venue of your choice when you book an event at Mahoney’s Bar & Grill.

Even the most discerning gourmet will be satisfied by the catering menu.

Shop for Unique Items at Earth House

Stop by Earth House if you’re looking for a place to shop for unique and distinctive items.

The Earth House’s proprietors designed it to make it the planet earth’s gift shop.

Its modest beginnings included low-watt light bulbs, shower water-saving devices, bumper stickers, and buttons.

Earth House is open all year long and offers the joyful tourists some cool apparel, candles, records, outlandish posters, and perhaps an old comic magazine or action figure.

Stop by the shop and admire its style and innovative features!

Pay a Visit to the Oceanair Himalayan Salt Cave

Oceanair Himalayan Salt Cave is a holistic health facility that provides a range of services and products to combat the harmful effects of contemporary living.

It is created, constructed, and run by North America’s leading Himalayan salt and building authorities.

All services and products are based on lovely, mineral-rich Himalayan salt.

They strive to provide you with the ideal fusion of art and science in a unique experience made just for you, whether you need to relieve tension or simply want to take a vacation.

For your comfort and well-being, the caverns have cutting-edge expertise and were expertly created to resemble the salt mines where halotherapy was first used.

Each Salt Cave Session lasts for 45 minutes.

Final Thoughts

The town of Orleans in Massachusetts makes for an idyllic weekend getaway, brimming with fascinating discoveries and thrilling outdoor exploration opportunities.

If you’re planning a trip to Orleans soon, don’t forget to reference this list for a memorable weekend getaway in this charming town.

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