Fun things to do in Orleans, Massachusetts! Includes beaches, hiking and biking trails, shopping, and the best restaurants in Orleans!

*A big thank you to the Cape Cod Chamber of Commerce for assisting us in our trip planning and arranging our visit to the Church Of The Transfiguration.*

About Orleans, Massachusetts

The historic town of Orleans, Massachusetts was settled in 1644 by Pilgrim colonists who had left Plymouth. The town wasn’t officially incorporated, however, until 1797. Today, Orleans is a great place to enjoy nature, eat, and shop.

Where is Orleans, Massachusetts?

So you might be asking, “Where is Orleans and how do I get there?” Well, Orleans is on the “Lower Cape” section of Cape Cod. This area is also affectionately known as the inner “elbow” of the Cape. Conveniently, it’s less than two hours south of Boston and is right off of US-6 E. If you’re flying to Cape Cod, there are regional flights to nearby Chatham and Provincetown.

Pro Tip: If you’re driving to Orleans, make sure you have these Road Trip Essentials! They include accessories, safety tips, and a printable checklist!

Fun Things To Do In Orleans, Massachusetts

Now, let’s take a closer look at some of the fun things to do in Orleans. Attractions will vary by season, but trust us when we say you can even find things to do in Orleans in winter!

Downtown Orleans

Downtown Orleans is cute and lined with tons of shops and boutiques that are independently owned. Shopping local is what it’s all about in this small town, with many of the stores having been around for over 50 years! You’ll find clothes, accessories, household items, and unique memorabilia.

Church Of The Transfiguration

Visiting the Church of the Transfiguration is definitely one of the best things to do in Orleans. No matter your faith, we recommend stopping in and taking a free tour of the church because it is truly exquisite. The hand-cut mosaics made of marble and glass and the hand-painted frescos will leave you breathless.

Guided tours are held Monday through Saturday (but not Wednesdays) from 10 a.m. to 4 p.m. and on Sundays following Eucharist. You can sign up for a tour on their website. Please note that this is a place of worship so when you visit, dress modestly and respect your surroundings.

*Due to the Covid-19 pandemic, tours are temporarily on hold*

Below is a video we made from our visit to the Church of the Transfiguration. It’s beauty is obviously best seen in person, but we hope this video gives you a better idea of how detailed and magnificent the church really is.

Orleans Beaches

Fun things to do in Orleans definitely includes visiting its beaches. Orleans beaches are beautiful and have won plenty of awards. Both Nauset Beach and Skaket Beach have won TripAdvisor’s Certificate of Excellence.

Nauset Beach is on the Atlantic ocean and was a Top 10 winner in the category of Best Massachusetts Beach, done by USA Today. Skaket Beach is located on Cape Cod Bay, so its waters are warmer and calmer. This has led Skaket Beach to be voted one of the best kid-friendly beaches in Cape Cod by Family Vacation Critic.

Other Orleans beaches we’d like to mention are South Orleans Beach on Pleasant Bay and Rock Harbor Beach. South Orleans Beach has scenic views of the bay islands and is perfect for sail boarding. Rock Harbor Beach is probably best known for its incredible sunsets.

things to do in Orleans includes visiting the Orleans beaches
Catching a sunset at the beach!

Hiking and Biking On Orleans Trails

There are so many hiking and walking trails in Orleans! Throughout Orleans, there are 13 established conservation areas. These areas are owned and maintained by either the Orleans Conservation Trust (OCT) or the Town of Orleans. If you’d like more information on individual conservation areas and trails, head over to OCT’s website. They include maps, trail distances, information on guided walks, and dog policies.

If you’re interested in biking trails in Orleans, the best is the Cape Cod Rail Trail. It’s over 25 miles long and passes right through the center of Orleans. You can get on the trail and head north towards Wellfleet or southwest toward Dennis. The rail trail was once a railroad line that has since been converted and paved.

Lots of great trails in Orleans!
Lots of great trails in Orleans!

Pro Tip: Make sure you read our Hiking Gear List For Beginners. It’s perfect for short hikes!

Coast Guard Motor Lifeboat CG 36500

Between the months of June and October, the historic Coast Guard Motor Lifeboat CG 36500 is docked in Rock Harbor, Orleans. You may recognize the boat and its story if you’ve seen the movie The Finest Hours.

The CG 36500 took part in an incredible rescue on the night of February 18, 1952. The tanker Pendleton had broken apart in a terrible 70-knot nor’easter snowstorm. Four Coast Guardsmen set out in the CG 36500, not really expecting to survive the mission. Remarkably, the four returned with 32 survivors!

CG 36500 has since been restored and is listed on the National Register of Historic Places. While it’s docked in Rock Harbor, visitors can take part in onboard Talks and Tours which are scheduled on summer weekends. Between the months of November and April, the boat is docked at Nauset Marine East.

Coast Guard Motor Lifeboat CG 36500 in Orleans
Coast Guard Motor Lifeboat CG 36500

Art Galleries

Orleans has been officially designated a Cultural District by the Massachusetts Cultural Council. Throughout town you’ll find art galleries and studios the feature local artists. Some popular galleries are By The Sea Driftwood Company (features gifts and home decor made of locally collected driftwood, shells, and beach glass) and Eastwind Gallery (a cooperative of award winning Cape Cod artists featuring oils, watercolors, pastels, acrylics, and photography).

By The Sea Driftwood Company
By The Sea Driftwood Company. Photo Credit: Cape Cod Chamber of Commerce

Best Restaurants In Orleans

There are a lot of great restaurants in Orleans! We loved the variety of cuisines and were thrilled that so many Orleans restaurants were open even during winter time.

Rock Harbor Grill

One of the best restaurants in Orleans is definitely Rock Harbor Grill. When we arrived for dinner, we were greeted with a big smile. We also appreciated the soft lighting and casual decor. It set the tone for our relaxed and cozy meal.

For our appetizer, we had the Devils On Horseback, which are medjool dates stuffed with sheep’s milk feta, wrapped in pecan wood smoked bacon, drizzled with reduced balsamic, and topped with fresh mint.

Rock Harbor Grill is known for their wood fired pizza, so of course we had to get one. We ordered the Mediterranean, which came with sun-dried & plum tomatoes, olives, roasted pepper, sheep’s milk feta, red onion, and a balsamic drizzle. Omg, the pizza was so good and we loved the crispiness of the bread.

Rock Harbor Grill is one of the best restaurants in Orleans and has the Devils On Horseback as an appetizer
Devils On Horseback
Mediterranean pizza from Rock Harbor Grill
Mediterranean pizza

Bangkok Thai Cuisine

Another great Orleans restaurant is Bangkok Thai Cuisine. Ever since our trip to Thailand, Vicky has been addicted to Pad Thai, so everywhere we go we try to get our hands on some. Bangkok Thai Cuisine certainly did not disappoint!

To start we had some Pork Dumplings, that were crispy and delicious. And then… Chicken Pad Thai! The noodles came with with egg, scallion, bean sprout, and were topped with ground peanut. We really enjoyed the flavors of this Pad Thai. Some places try to add extra ingredients that just aren’t necessary, but Bangkok Thai Cuisine got it right!

Pork Dumplings from Bangkok Thai Cuisine
Pork Dumplings
Chicken Pad Thai from Bangkok Thai Cuisine one of the best restaurants in Orleans
Chicken Pad Thai

Sunbird Cape Cod

While talking to some locals, we got the suggestion to stop by Sunbird. It’s another of the best restaurants in Orleans. This bright, cheerful, and modern cafe grew from of a popular food truck. They serve seasonal, locally sourced food and have a great coffee selection as well.

During our visit we had a Grilled Cheese Sandwich (we added bacon) and a side of Fried Potatoes. You guys, that grilled cheese was amazing. The bread was so buttery and thick and the mozzarella was the perfect amount of melt in your mouth. Even with how much we loved it, we could only eat half because of how big it was. The potatoes were really good too. They had a nice crunch and just the right amount of salt and seasoning.

Grilled Cheese Sandwich from Sunbird one of the best restaurants in Orleans
Grilled Cheese Sandwich
Fried Potatoes from Sunbird
Fried Potatoes

Hot Chocolate Sparrow

If you’re craving some sweet treats, we recommend visiting Hot Chocolate Sparrow. They have hand-dipped chocolates, pastries and desserts, and coffee from around the world. It’s also a great place to meet up with friends and catch up, which is exactly what we did.

We met up with a fellow house sitter and chatted while we had a divine mocha latte and a fresh-baked flaky croissant filled and drizzled with warm chocolate. Yum!

yummy chocolates from Hot Chocolate Sparrow
So many yummy chocolates!
Mocha latte and a Chocolate Croissant from Hot Chocolate Sparrow
Mocha latte and a Chocolate Croissant

Cottage Street Bakery

Another local favorite is Cottage Street Bakery. They are probably best known for their Dirt Bombs, which are basically cinnamon sugar donuts in muffin form. Apparently, when seasonal visitors come back to the Cape each year, their first stop is the Cottage Street Bakery for a Dirt Bomb. Even though we’re not huge fans of cinnamon, we really enjoyed our Dirt Bomb and it paired really well with the locally roasted coffee we got there as well.

And although they have all kinds of breads, pastries, and cookies, we need to really highlight their cakes. We had a chocolate cake made for Mark’s birthday and it was almost too beautiful to eat. Almost. The chocolate layers and chocolate icing were perfect and every bite was sinfully delicious.

Coffee and Dirt Bomb from Cottage Street Bakery
Coffee and Dirt Bomb
chocolate cake from Cottage Street Bakery
Amazing chocolate cake!

Where To Stay In Orleans

We were house sitting during our stay on Cape Cod, so we didn’t stay in any hotels or B&Bs in Orleans. However, there are a few charming historic inns that come highly recommended:

If you’d rather stay in a house, you can also check out these popular Airbnb stays in Orleans.

Pro Tip: Would you like to travel with free accommodation? Learn how you can get started house sitting!

Final Thoughts On Things To Do In Orleans

Orleans is a great town. We love the emphasis on supporting local businesses and how much there is to do outdoors. And, of course, all of the great restaurants. We definitely recommend you pay Orleans a visit. And if you’re sticking around Cape Cod, we also suggest a day trip to Martha’s Vineyard and visiting the cute town of Sandwich.

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Fun things to do in Orleans, Massachusetts! Includes beaches, hiking and biking trails, shopping, and the best restaurants in Orleans!