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Chatham & Orleans, MA Guide

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About Chatham & Orleans

With beautiful beaches, harbors, and pedestrian-friendly downtowns, Chatham and Orleans, Massachusetts, offer visitors a classic Cape Cod experience. From historic Chatham Light or the natural beauty of the Monomoy National Wildlife Refuge, to eclectic shops in the village centers, Chatham and Orleans provide visitors a chance to enjoy a slower pace on the Cape.

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Chatham Hood Bikes

Chatham Hood Bikes mini hero image

Chatham Hood Bikes is your place to rent and service bicycles while vacationing on Cape Cod.  We have two new locations in Chatham so come visit us at…

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  • +1 508-469-0210
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  • 400 Main Steet, Chatham, MA

The Sparrow Store

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Unique Gifts • Cool Things

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  • +1 508-255-9400
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  • 26 Main Street, Orleans, MA

Gustare Oils & Vinegars

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Welcome to Gustare Oils and Vinegars, where you will enjoy a unique tasting experience by sampling imported extra virgin olive oils and balsamic…

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  • +1 508-945-4505
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  • 425 Main Street, Chatham, MA

Nauset Marine

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Nauset Marine offers an assortment of Powerboats for Full or Half Day Rentals. Ranging from 19’ to 22’, All our boats are equipped with Coast Guard…

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  • +1 508-255-0777
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  • 45 Route 6A, Orleans, MA

Designs by S&R

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Inspired by the beauty of Cape Cod, Designs By S&R is a local jewelry shop in Orleans, MA that specializes in handcrafted and custom jewelry. 

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  • +1 508-240-3608
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  • 85 Route 6A, Orleans, MA

Thompson's Printing

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Welcome to Thompson's Printing, Inc., a state-of-the-art full service commercial printing facility conveniently located on Finlay Road in Orleans…

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  • +1 508-255-0099
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  • 51 Finlay Road, Orleans, MA

Chatham Cookware Cafe

Chatham Cookware Cafe mini hero image

Low-key bakeshop providing coffee & pastries, sandwiches & salads, plus outdoor seating.

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  • +1 508-945-1250
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  • 524 Main Street, Chatham, MA

Church Of The Transfiguration

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The Church stands at the center of the Community of Jesus, an ecumenical monastic community in the Benedictine tradition. Worship services include…

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  • +1 508-255-1094
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  • 5 Bay View Drive, Orleans, MA

Chatham Seaside Links Golf Course

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Gold Course and Country Club overlooking the Atlantic Ocean in Chatham MA

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Snow's Home & Garden

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ABOUT US Find It at Snow’s Expert advice, quality products and good old fashioned customer service.

For more than 130 years, Cape Cod locals and…

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  • +1 508-255-7214
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  • 53 Finlay Road, Orleans, MA

The Chatham Cheese Company

The Chatham Cheese Company mini hero image

he Chatham Cheese Company is a gourmet food shop featuring artisanal cheeses from around the world. In addition to cheese, we also carry a great…

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The Cove Motel

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For more than forty years, The Cove has been a landmark on Cape Cod. A waterfront motel, noted for its outstanding comfort and quality; an ideal…

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  • +1 800-343-2233
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  • 13 Route 28, Orleans, MA

Local Colour Resale Boutique

Local Colour Resale Boutique mini hero image

Welcome to Local Colour Resale Boutique, 
the best kept secret on Cape Cod for women's clothing and 
  accessories! 

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  • +1 508-255-2846
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  • 9 Cove Road, Orleans, MA

The Queen Anne Inn & Restaurant

The Queen Anne Inn & Restaurant mini hero image

Welcome to the "Queen Anne Inn" one of Cape Cod's most beautiful and original full service inns; owned and operated by the Weinkopf family since 1979…

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Yellow Umbrella Books

Yellow Umbrella Books mini hero image

This is no ordinary book store

What is often missed in today's book-selling environment can still be found at Yellow Umbrella Books - a place…

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  • +1 508-945-0144
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  • 501 Main Street, Chatham, MA

Stick 'n Rudder Aero Tours

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Stick'n Rudder Sightseeing tours is now offering biplane rides in our 2 passenger classic Waco Bi-Plane. Experience the heart pounding, wind in your…

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Chatham Fish & Lobster

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Chatham Fish & Lobster

Stop in and visit Paul and Eileen at Chatham Fish & Lobster where you will find the freshest, highest quality seafood caught…

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  • +1 508-945-1173
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  • 1291 Main Street, Route 28, Chatham, MA

Yale New Haven Health - Sky Health

Yale New Haven Health - Sky Health mini hero image

SkyHealth emergency patient transport helicopter is staffed by highly skilled medical professionals, including a critical care flight nurse and a…

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Chatham Village Cafe/Chatham Bakery

Chatham Village Cafe/Chatham Bakery mini hero image

Remember the excitement of going to your local bakery when you were a kid 
and standing in front of the bakery case trying to decide which treat to…

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  • +1 508-945-2525
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  • 69 Crowell Road, Chatham, MA

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Chatham Candy Manor

Chatham Candy Manor mini hero image

Our Chocolate

What is the secret to making chocolates so incredible that people have been coming from all over the country to a small picturesque sea…

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  • +1 508-945-0825
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  • 484 Main Street, Chatham, MA

Chatham Chamber of Commerce

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Chatham is located on the elbow of Cape Cod surrounded on three sides by water.  Located halfway between Falmouth and Provincetown, it extends out to…

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Wireless Zone

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Verizon Wireless Zone: Ranked highest in Customer Satisfaction by Verizon in 2011, 2012, 2013, 2014 and 2015, we're proud of our knowledgeable &amp…

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  • +1 508-255-5557
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  • 169 Route 6A , Orleans, MA

The Yardarm Restaurant

The Yardarm Restaurant mini hero image

Welcome to The YARDARM

Orleans, MA

Serving: Lunch, Dinner, Sunday Brunch

The Yardarm has been an Orleans landmark for residents and 

visitors…

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  • +1 508-255-4840
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  • 45 Route 28, Orleans, MA

St. Christoper's Gift & Consignment Shop

St. Christoper's Gift & Consignment Shop mini hero image

St. Christopher’s Gift & Consignment Shop is known as a destination for anyone looking for a wide variety of quality merchandise in excellent…

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  • +1 508-945-2211
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  • 637C Main Street, Chatham, MA

Ship's Knees Inn

Ship's Knees Inn mini hero image

A Cape Cod Bed and Breakfast just 1/4 mile from Nauset Beach (the southernmost beach on the Cape Cod National Seashore)! Enjoy the warmth and charm of…

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Lake Farm Kennels

Lake Farm Kennels mini hero image

Our facility is family owned and operated. We have been in business for over 35 years and, as one of the longest operating Kennels on Cape Cod, we…

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  • +1 508-255-7214
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  • 53 Finlay Road , Orleans, MA

Tommy Dixon Collections and the Cook's Nook

Tommy Dixon Collections and the Cook's Nook mini hero image

Tom Peters and Ron Baird owned a bed & breakfast in Rehoboth Beach, DE for eight years, wintering on Sanibel, FL to get away from the freezing storms…

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  • +1 508-945-1225
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  • 610 Main Street, Chatham, MA

A Great Yarn

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A Great Yarn is a charming little nook in beautiful downtown Chatham, Massachusetts. Come snuggle up in one of our cozy window seats and enjoy a cup…

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  • +1 508-945-5605
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  • 894 Main Street, Chatham, MA

Whalewalk Inn & Spa

Whalewalk Inn & Spa mini hero image

Welcome to The Whalewalk Inn & Spa

Get away from the hustle and bustle of your everyday life and come relax at our romantic & secluded bed and…

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Chatham Conservation Foundation Walking Trails

Chatham Conservation Foundation Walking Trails mini hero image

The Chatham Conservation Foundation preserves land for the benefit of the people, plants, animals, and ecosystems of Chatham. 

It is a non- profit…

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  • +1 508-945-4084
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  • 104 Crowell Road, Chatham, MA

The Orleans Chamber of Commerce

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The Orleans Chamber of Commerce is the recognized essential organization that builds, promotes and supports the Orleans business community through…

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  • +1 508-255-1386
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  • 8 Eldredge Park Way, Orleans, MA

Friends Marketplace

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About Friends’ Marketplace Friends’ Marketplace and Garden Center is an award winning independently owned grocery store and full-fledged outdoor…

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  • +1 508-255-0963
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  • 57 Main Street, Orleans, MA

Rodeway Inn

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The Rodeway Inn is located midway between spectacular Nauset Beach and Skaket Beach. The centrally located Rodeway Inn is the perfect base for your…

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Lighthouse Beach Yoga

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Begin your day with a loving kindness Kripalu yoga class that integrates breathing/pranayama, asana/postures, relaxation, and meditation; on Cape…

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  • +1 508-945-7643
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  • 37 Main Street, Chatham, MA

Guapo's Tortilla Shack

Guapo's Tortilla Shack mini hero image

 

Guapo’s Tortilla Shack is a casual, Baja-style tortilla shack serving the best darn fish tacos this side of the Bridge.   Easily accessible…

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  • +1 508-255-3338
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  • 136 Route 6A, Orleans, MA

Rock Harbor Grill

Rock Harbor Grill mini hero image

The Rock Harbor Grill is all about great food prepared with fresh, quality ingredients with a passion for flavor and style! Owner Chuck Konner and…

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  • +1 508-255-3350
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  • 18 Old Colony Way, Orleans, MA

Pleasant Bay Village Resort

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Frommer’s New England Said… “Owner Howard Gamsey is a prodigious gardener: Over the past quarter-century, he has transformed what was an ordinary…

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Hole in One Breakfast & Lunch/ Fairway Restaurant & Pizza

Hole in One Breakfast & Lunch/ Fairway Restaurant & Pizza mini hero image

 

To walk into the Hole In One donut shops and eateries in North Eastham and Orleans is like coming home. Family, friends, builders, bankers…

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  • +1 508-255-3893
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  • 98 Route 6A, North Eastham, MA

Bird Watcher's General Store

Bird Watcher's General Store mini hero image

Bird Watcher's General Store is the original birding store, the first ever. It remains the largest shop dedicated to birding and bird feeding. We…

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  • +1 508-255-6974
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  • 36 Route 6A, Orleans, MA

Hot Chocolate Sparrow

Hot Chocolate Sparrow mini hero image

We are busier than ever hand-dipping chocolates daily for our busy espresso and dessert bar. The Hot Chocolate Sparrow, Cape Cod's most popular…

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  • +1 508-240-2230
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  • 5 Old Colony Way, Orleans, MA

Coastal Craft Gallery

Coastal Craft Gallery mini hero image

Welcome to Coastal Craft Gallery 

A co-operative gallery of artists who work and live year-round on Cape Cod

 

Everything you find in our shop is…

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  • +1 508-255-0220
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  • 246 Main Street, Orleans, MA

Canterbury Leather

Canterbury Leather mini hero image

A Huge selection; Sheepskin, Luggage, Jewelry, Jackets, Hats, Handbags, Briefcases, Belts, Ugg, Teva, Sorel, Sebago, Naot, Minnetonka, Mephisto, Keen…

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  • +1 508-255-4542
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  • 640 Main Street , Chatham, MA

Jomama's NY Bagels

Jomama's NY Bagels mini hero image

We are committed to offering you fresh, delicious & wholesome food, great coffee and drink, a cool and relaxing atmosphere and a smiling face when you…

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  • +1 508-348-5621
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  • 400 Main Steet, Chatham, MA

Corner Store

Corner Store mini hero image

COME ON BY

Our customers come in hungry and leave smiling. We strive to make the best burritos, panini, sandwiches, soups, cookies and whoopie…

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STLK, Inc. Building and Remodeling

STLK, Inc. Building and Remodeling mini hero image

Your satisfaction is our satisfaction

Who can you trust to take care of your building projects? For more than 35 years, we've been building and…

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Chatham Shark Center

Chatham Shark Center mini hero image

The Chatham Shark Center™ offers an in-depth look at one of the ocean's most magnificent and misunderstood species: the Great White Shark! Through…

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Wheelhouse Bike Co.

Wheelhouse Bike Co. mini hero image

WHEELHOUSE BIKE Co. is a full-service bike shop located by the bike path in Chatham Vilage. We have every kind of bike you need for your Cape Cod…

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3 Fools

3 Fools mini hero image

Pizza • Wings • Gyros • Falafel • Salads • Subs • Sandwiches • Soups • Dinner Specials

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The Black Dog

The Black Dog mini hero image

Out of one sailing Captain's love for the sea, his island home, and of course, his dog, The Black Dog Brand was born.

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The Montgomery Financial Group

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  • Investment Strategy & Management
    We are independent, fee-only advisors; we advise, we don't sell.






  • Social Security & Retirement Income Strategies
    …

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Ridgevale Beach Snack Bar & Boat Rentals

Ridgevale Beach Snack Bar & Boat Rentals mini hero image

FAMILY OWNED AND OPERATED RENTALS, WATER ACTIVITIES, TOURS, LESSONS, AND BEACHFRONT SNACK BAR 

Our family has been sailing these waters since…

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Chatham Penny Candy

Chatham Penny Candy mini hero image

A Fun, Old-Fashioned Candy Store filled 
with the Nostalgic Candy Treats 
of the 50s, 60s & 70s!

Every piece of candy will transport you back to your…

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Oceana

Oceana mini hero image

Your Port of Call for Shopping On-Cape! A family owned, local shopping experience that is second to none. Find jewelry, home decor, personal items and…

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Sea Bags

Sea Bags mini hero image

t Sea Bags we design and handcraft tote bags and accessories from recycled sails that have sailed around the world. Once a sail, forever a Sea Bag.

…

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Bangkok Cuisine

Bangkok Cuisine mini hero image

GREAT TASTE AT 7 DIFFERENT LOCATIONS Bangkok Cuisine offers you the best Thai food on Cape Cod for locals and for visitors who travel from afar.…

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Sweet Tomatoes Pizza - Chatham

Sweet Tomatoes Pizza - Chatham mini hero image

Welcome to Sweet Tomatoes! At Sweet Tomatoes, we offer: Pizza - Calzones - Pasta - Fresh Salads - Sandwiches Burritos - Subs - Wraps - Pizza by the…

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Lighthouse Beach Yoga

Lighthouse Beach Yoga mini hero image

Begin your day with a loving kindness Kripalu yoga class that integrates breathing/pranayama, asana/postures, relaxation, and meditation; on Cape…

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Couvé at Chatham Inn Relais & Chateaux

Couvé at Chatham Inn Relais & Chateaux mini hero image

A Fine Dining Destination “GLOBALLY INSPIRED, LOCALLY ACQUIRED”

Enjoy an evening of the finest food and exceptional service at Cape Cod’s Only…

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Corner Store

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Corner Store

FRESH. FAST. FUN.

   

This is not your average store. From the outside it may look…

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Chatham Works

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FitnessOur Fitness Philosophy

We believe that some of the best reasons to exercise have absolutely nothing to do with your appearance, and that a…

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Chatham Tides

Chatham Tides mini hero image

Enjoy the peaceful tranquility of our beachfront hotel on Cape Cod in Chatham, Massachusetts. Experience picturesque ocean views from your very own…

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Chatham Village Market

Chatham Village Market mini hero image

From the very start, when the Chatham Village Market began in July of 2003 at the location of the former Chatham A&P, there has been a dedication to…

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Oceanair Himalayan Salt Cave

Oceanair Himalayan Salt Cave mini hero image

Committed to Holistic Healing & Heath

Oceanair's large, open cave is made with pink Himalayan salt and breathe in microscopic salt particles that can…

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Honey Candle Co.

Honey Candle Co. mini hero image

 

At honey candle we make 100% beeswax and bayberry candles, all our wax comes from american beekeepers, by purchasing our candles you support…

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Orleans Dermatology

Orleans Dermatology mini hero image

Orleans Dermatology & Laser Therapies is committed to providing readily accessible high quality skin care to the Cape community. We serve the folks of…

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