This charming enclave at the elbow of Cape Cod has a little something for everybody

If you view Cape Cod from space, its distinctive flexed and slightly bent arm reaches out, into the Atlantic Ocean, almost as a hook, to ensnare passing fish, ships and all lovers of the quintessential treasures found throughout the region. Nestled in the elbow of this unique topographic icon is the village of Orleans. At the heart of Orleans beats the artery of the village—Main Street. No other town on the Cape has a Main Street that runs in a straight line between the calm waters of Cape Cod Bay and the powerful intensity found in the open Atlantic Ocean. Spanning just over four miles, one end of Main Street finds the serenity of Rock Harbor, with its endless sand flats that welcome countless recreational clam diggers. The harbor’s iconic “Clam Trees,” that are placed every summer as one of the most unique navigational aides ever conceived, are also the subject of local lore recounting the shell-fishermen who used to deposit clams and quahogs at the base of the trees on their way into shore. The next season the “planted” mollusks would have multiplied, resulting in a rich harvest. Since Rock Harbor is a serious working harbor, commercial fishing boats and recreational motor craft are a year-round sight.

As Main Street approaches downtown, one of the first establishments encountered is Snow’s Home and Garden. One of the first settled families on Cape Cod, the Snows have called the region home since 1644. In 1887, William and Annie Snow opened the first official Snow’s store. They are still providing Cape families and visitors with anything they could ever need to make you feel right at home. Next door, Mahoney’s Atlantic Bar & Grill showcases owner/chef Ted Mahoney’s upscale interpretation of a Boston bistro meets Cape Cod Main Street. A lively bar and a cozy dining room serve up a thoughtful list of craft cocktails and delicious cuisine, all under the roof of a historic 19th-century building.

Next door, Watson’s Men’s Store has been dressing customers for generations. Current owners Dan and Lynn Eberly are thrilled to be the latest stewards of the venerable clothier that has been around for almost seven decades. Lynn says customers repeatedly tell them that they never realized there was a large parking area, as well as a rear entrance behind the store. 

To miss that convenience would also miss one of Orleans’ hidden gems. Behind Watson’s, and their neighboring businesses on Main Street, as well as one block of businesses around the corner on Route 6A, is the pearl in the Orleans oyster. A large parking area is flanked on all sides by countless businesses that might otherwise go unnoticed. Starting at the corner shared with Mahoney’s is the Coastal Craft Gallery, a melange of ceramics, photography, jewelry and other crafts by local artists. Next door Oceana, whose tagline is “Inspirations with an accent on design,” presents a perfectly curated selection of home accessories, gifts, art and jewelry that are all inspired by the sea. Owner Jane Williamson gave the entire store a subtle facelift in the spring of 2018, so that the bright airy space showcases unique and unexpected finds in their very best light. One stop at Oceana will have you back again, and again and again. Across the parking lot, tucked into the corner are two art galleries full of exceptional work by local artists. East Wind Gallery not only has a myriad of work on display, but the various artists represented are often found working in the on-site studio. Gallery 31 Fine Art represents a cadre of distinctive artists with international acclaim. Their robust schedule of events, demonstrations and talks provide access to an impressive variety of world-class creators.

Just a few doors down, the popularity of Eastham’s Hole in One prompted a second location to open in Orleans several years back. Their breakfast and lunch offerings, as well as the bakery and endless donut selections, are perfect to grab on the go, sit and enjoy on site, or pack up for a boating, beach or biking picnic. Orleans does not lack for dining options—across the street, the iconic Land Ho! Restaurant has been serving up burgers, sandwiches, salads, seafood and even a sizzling steak or two for years. Truly considered a landmark in the town, it is a place to soak up authentic local color.

A short distance away down Cranberry Highway, the Lobster Claw Restaurant has been serving families the freshest seafood around for over 50 years. Open seasonally, their relaxed style doesn’t detract from the main event—seafood. Down the street on the picturesque Town Cove, the Orleans Waterfront Inn and Restaurant boasts rooms with a view as well as sun-filled dining room that offers views that span the breadth of the charming cove-front. Their award-winning menu highlights local delicacies in innovative ways. Bonus: The inn is purported to be haunted, so an exciting adventure is always a possibility.

Back at the center of town, the shopping continues with Kid & Kaboodle, a children’s clothing store where finding the perfect outfit for a family portrait or a gift for a new addition is easy. Gift-wrapping, shipping, registry and personal shopping are just some of the ways this full-service clothing store has earned the loyalty of their customers through the generations.

If you still haven’t found something to satisfy your hunger, the Corner Store, the hugely popular burrito and sandwich shop in Chatham, has a new location right on Main Street in Orleans. Their innovative daily specials, like a buffalo chicken, mac and cheese burrito, will get you scratching your head and rubbing your belly. A stop at either Corner Store isn’t complete without one of their famous whoopee pies in a variety of seasonal flavors. 

Across the street, Ragg Time, a comfortable and stylish women’s clothing store, carries brands like the popular British label Joules.  Their selection of comfortable, coastal-inspired lines will have you settling down with a straw hat, a good book and a warm breeze in no time. A few doors down, lovers of women’s shoes, and everything else that goes along with them, will get their fix at If the Shoe Fits. This hip and casual boutique will put a bounce in your step with their fun and flirty fashion that somehow seems to have something for everyone. Not only do they have shoes for every occasion and season, but the carefully curated pieces will also guarantee you some compliments.

Orleans is full of hidden gems, but perhaps none more perfectly so than a small consignment shop, named Hidden Gem Cape Cod, tucked into a quiet courtyard at 47 Main Street. For whatever reason, Orleans has a bounty of consignment shops, some clothing based and some, like this one, offer a variety of small furniture and accessories. With the tagline, “A consignment store with a sense of humor,” owner Anne Kiefer says that she can always find something interesting about the variety of items brought to her for consignment. Shoppers can expect to find a few vintage items and most certainly something they may have never thought they needed.

For the things you know that you need, Friends’ Marketplace is the kind of grocery store, butcher, wine purveyor and farm stand every community should be so lucky to enjoy. They say that they are a community-centered, food-focused market with local flavor and big tastes. One visit will confirm those statements for most anyone.

Main Street continues on its journey to the other sea as it enters the village of East Orleans. A smaller yet equally rich collection of shops and dining options exists in this outpost on the way to Nauset Beach. Adorn, a charming shop imagined by a young, talented jewelry designer, Molly Avellar, invites visitors in to peruse the work of over 80 different artisans, most local and of the ones not, most are free-trade. Everything from art to ceramics, to keepsakes and jewelry, including Avellar’s beach-inspired unique pieces, is sure to tug at your heart and soul, begging to become a permanent part of your Cape tapestry.

Blue Claw Boat Tours leaves out of East Orleans as they take adventurers out for seal tours and public and private cruises along the coastline and to the intrepid Monomoy Island that sits between Orleans and Chatham.

After a day on the water, stop for a meal at the Barley Neck Inn, situated in the fork of Barley Neck Road and Beach Road. This posh bistro is housed in an 1848 sea captain’s home and serves up award-winning cuisine, a full bar and a raucous schedule of live entertainment.

Finally at the end of the road, after passing many a real estate sign for Beach Road Properties—a real estate firm who despite the Cape’s limited inventory has a lot to offer—the journey ends where the land does as well, Nauset Beach. Recent storms have taken their toll on this iconic spot known worldwide for it crashing surf, and never-ending stretches of miles of wide beach. This is where old Cape Cod and today’s Cape meet. The old Philbrick’s snack bar succumbed to a storm in 2018 and now food trucks with innovative culinary interpretations try to take up the slack. The wide, flat beach, absent of the dunes found farther up the coast, has been augmented with a manmade protective berm that is intended to protect this precious resource for the future. You may not be able see the waves, and imagine the distant shore of far away countries, as you enter the parking lot, but the beautiful Nauset Beach sand is still the same, the beachgoers have rarely changed at all, and the sun still dances with a million diamonds on the endless sets of perfectly formed waves. Not a bad dead end for a special Main Street.

Visiting the Village

Adorn

Adorn offers a carefully curated selection of handcrafted jewelry, art, gifts and unique goods for home and lifestyle with a focus on featuring independent designers, artists and handmade brands based locally on Cape Cod and throughout the United States. Find Adorn on the way to Nauset Beach.

211 Main Street, East Orleans. 774-316-4245. AdornCapeCod.com

Barley Neck Inn

The Barley Neck Inn is a local favorite in Orleans on the way to Nauset Beach. A wonderful choice for a family-friendly dinner, cocktails, Sunday brunch, rehearsal dinners, and special events. With an award-winning wine list and live music on the weekends, the BNI is your year-round destination!

5 Beach Road, East Orleans. 508-255-0212. barleyneck.com

Beach Road Properties

Located in the heart of downtown Orleans. Beach Road Properties’ knowledgeable team is here to assist you in fulfilling your dreams of owning a home on Cape Cod or planning the perfect vacation getaway. Family owned and operated for over 20 years. Beach Road Properties looks forward to working with you!

41 Main Street. 508-255-5444. BeachRoadCapeCod.com

Blue Claw Boat Tours

Salt air and balmy summer breezes roll over the sand dunes of Nauset Beach. Gulls circle as seals pop up in wonder. Sunshine sparkles off the water as your captain guides you through the creeks and bays of pristine Pleasant Bay. 3 USCG boats/captains, with public and private tours.

Departs from Nauset Marina, 235 Main Street. 508-240-5783. blueclawboattours.com

Corner Store

Best Lunch voted by Cape Cod LIFE readers! 2 Cape Cod locations (Orleans & Chatham). Visit the center of Orleans for Burritos, Salads, Local Beer, Wine, Coffee, Cookies and Whoopie Pies! Build your own custom burrito or choose from the menu.

54 Main Street. 508-255-5454. The Corner Store is FreshFastFun.com

Friends’ Marketplace

Friends’ Marketplace is a community-centered, forward-thinking grocery store that has been a mainstay in Orleans for over 20 years. This family-run business offers an incredible selection of everyday and natural items, chef-prepared ready-to-go foods, an in-house butcher, organic produce, a gourmet deli, bakery and beautiful outdoor garden shop.

57 Main Street. 508-255-0963. friendsmarketplace.net

Gallery 31 Fine Art

Gallery 31 Fine Art, celebrating its 20th year, offers representational and interpretive fine art of the sea, shore, bog, bay and classic still life paintings. Receptions, gallery talks and painting demonstrations provide opportunities to engage with artists. Visit the gallery and experience why it’s often called “the art collector’s jewel.”

34 Main Street Square. 508-208-6703. gallery31capecod.com

Hidden Gem

Experience consignment with a sense of humor at Hidden Gem. Visitors can expect the unexpected, with an eclectic array of vintage Americana, Asian and quirky collectibles as well as locally made crafts. Antique tools and housewares and vintage jewelry are among the many gems you’ll discover. Open year-round, Monday through Saturday, 10–4.

47 Main Street. 774-801-2667. hiddengemcapecod.com

Hole In One

Eat where the locals do and indulge your taste buds in the mouthwatering delights of Hole In One. Homemade baked goods include their signature hand-cut donuts, moist, flaky, and simply irresistible, with fun varieties like glazed sour cream and toasted coconut crunch. Stop in for a hearty full-service breakfast or lunch in their new solarium.

98 MA Route 6A (also in Eastham). 508-255-3740. theholecapecod.com

If The Shoe Fits

Established in 2002, If The Shoe Fits specializes in “not so easy to find” shoes, clothing and accessories, bringing to the Cape collections from new designers with a fresh look at new trends for all ages. Knowing shopping for a specific occasion can be daunting, If The Shoe Fits provides personal customer service.

47 Main Street (also located on Main Street, Chatham). 508-348-1926. iftheshoefitsonthecape.com

Kid & Kaboodle

One of New England’s largest children’s boutiques, Kid & Kaboodle offers unique clothing, shoes and gifts for boys and girls, sizes infant to 16. Find the perfect gift, special occasion outfit or everyday essentials. A subsidiary,  cribrentalscapecod.com, offers baby equipment and beach gear rentals. Voted Best Children’s Clothing Shop since 2002!

115 MA Route 6A. 508-240-0460. kid-kaboodle.com

Lobster Claw

Voted Best Family Dining Restaurant perennially by Cape Cod LIFE readers, the Lobster Claw serves fresh local seafood, delicious steaks, chowders, early-bird specials and take-out. Celebrating the restaurant’s 50th anniversary, the Berig family will warmly welcome you! A function room and gift shop are available.

42 Route 6A. 508-255-1800. lobsterclaworleans.com

Oceana of Orleans

Your Port of Call for shopping on-Cape! Family-owned, Oceana of Orleans is a must-visit, offering an immersive shopping experience you won’t forget. Filled with exquisite jewelry, beautiful home decor, fun clothing, toiletries and so much more, all inspired by the ocean and seaside living.

1 Main Street Square. 508-240-1414. oceanacapecod.com

Orleans Waterfront Inn

Orleans Waterfront Inn offers fresh seafood and a delicious, diverse menu in an elegant dining room, casual pub and a beautiful outdoor deck, all overlooking picturesque Orleans Town Cove. Serving lunch, dinner and Sunday brunch. Weddings and special events are a specialty. Welcoming guest rooms and suites available. Open May-September.

3 Old County Road (just off Route 6A). 508-255-2222. OrleansInn.com

Ragg Time

Ragg Time Ltd is known for casual, comfortable women’s clothing, made using natural fibers and offered in a variety of prints, solids and stripes. Shop Ragg Time for bathing suits, summer dresses, shorts, skirts and much more! Ragg Time strives for apparel made in the USA. Open seven days a week year-round.

43 Main Street, Orleans Center. 508-240-0925. raggtimeltd.com

Watson’s Men’s Store

Formalwear, Sportswear, Resortwear, Ruggedwear. Over 68 years offering quality goods and service. Customers say: “There’s no place like Watson’s!” Cape Cod’s most complete selection of men’s clothing and accessories year-round. See, touch and try on over 80 quality brands at great prices with brand-smart service in a friendly, resort-style, feel-good store.

34 A Main Street. 508-255-3003. watsonsstyle.com