Shopping and Dining

In downtown Osterville, MA, you’ll find everything you need, from a fascinating mix of retail shops to a great selection of renowned restaurants. Spend the day and visit our boutiques, gift shops, antiques shops, and art galleries. Stay for lunch or dinner or enjoy take-out from one of our many fine dining establishments.


RAINBOW'S END, Main Street(508) 428-5304

RAINBOW’S END CONSIGNMENT SHOP is a retail store owned and operated by our church. It is open every week on Wednesday through Saturday from 10 AM to 3 PM. We accept donations and consignments. We sell everything from jewelry to large furniture pieces. All donations are tax deductible. Lillian Delmore is our manager. She will be pleased to assist you. Proceeds from sales go to support the missions and ministries of our church.


Creative Hands Gallery, 812 Main Street, Unit 2(774) 521-4304

For More information visit our website

OSTERVILLE ART GALLERY, 8 West Bay Road | (508) 428-5830




 IRRESISTIBLES, 25 Wianno Ave. | (508) 428-1936 

Irresistibles opened its first store in Boston’s Faneuil hall in 1977.  Since then the merchandise mix has evolved from accessories to a collection of well-designed and colorful women’s clothing, jewelry and accessories. Irresistibles carries collections from Nic and Zoe, Christopher Blue, Trina Turk, Tommy Bahama and so many more.

Hours: Mon-Sat. 10:00am-5:00pm starting Sundays April 3rd 12:00-4:00pm


KATHERINE, 832 Main Street | (508) 681-2288

katherine is a luxury home decor, clothing, jewelry and accessories boutique.  We feature home decor by Jonathan Adler, Vietri dish wear, inhabit and Oyuna cashmere sweaters and robes, Matta clothing, jewelry by Spinelli Kilcollin, gorgeous coffee table books from Taschen and Assouline, Omersa hand crafted footstools from England, and Oliver People’s sunglasses in addition to other unique items for the kitchen, bath and home.


Lilly Pulitzer, 13 Wianno Ave. (774) 228-2985

Hours: Mon-Sun 10am - 6pm


POCKET FULL OF POSIES INC., 7 Wianno Ave.(508) 420-8895

At Pocket Full of Posies, we delight in helping you find the perfect fit for your family! A children's shop nestled in the heart of Osterville, we carry many companies and varieties of clothes, toys, and accessories for boys and girls from their first moments to their growing years in sizes from new born to 14. We specialize in high end, high quality garments that make perfect gifts too!

Because every article in a child's wardrobe should be as unique as they are, we offer custom monogramming for any of our products. We offer many custom and specialty items and are always willing to order an item that meets your specifications if we don't have any in stock! At Pocket Full of Posies we make sure we do our part to preserve our beautiful planet. We recycle all our packaging and waste and use recycled bags and furniture in our store. We are always happy to serve you and appreciate your patronage!

We will gladly gift wrap your item at no extra charge. Call to order custom monogramming!


SARA CAMPBELL, 846 MAIN STREET | (774) 361-8372

Sara Campbell's classic apparel appeals to women of all ages, truly proving that great style is timeless. Her loyal shoppers visit for a unique selection of sportswear and specialty dresses with thoughtful trims and finishes. Headquartered in Newmarket Square in Boston, the brand operates 25 bricks and mortar boutiques along the east coast and midwest. Sara Campbell is known for her philanthropic efforts and manufacturing in the USA.


THE SHOE SALON, 837 Main Street(508) 428-2410

The Shoe Salon is a family run business that has been a part of Cape Cod’s landscape for more than a quarter of a century with locations in Osterville, Mashpee and Chatham. These renowned shops are where you will find the latest from Cole Haan, Kate Spade, Stuart Weitzman, Zalo, Mephisto and others in a warm and welcoming environment. In addition to the wonderful selection of shoes, the Shoe Salon also carries a unique line of sweaters, handbags and other accessories.

Hours: Monday-Saturday 10:00am-5:00pm, Sunday 11:30-4:00pm



MAHONEY’S, 2929 Falmouth Road(508) 420-4428

Full service garden center, we are dedicated to providing the highest quality and largest selection of garden plants, gardening products and gardening services.



FANCY’S MARKET, 699 Main Street(508) 428-6954

At Fancy’s Market you will find an exceptional butcher department, delicious produce, a fabulous selection of wines, beer, and liquor, fine cheeses, and fresh-baked goods. An award-winning deli department serves an enticing array of prepared entrees and kitchen salads, as well as sliced meat and cheese, and a wide array of classic subs and hot sandwiches. Catering is available through Fancy’s as well- talk to our staff in the kitchen about your specific needs and allow them to help you plan your special event.

Hours: Everyday 7:00am – 7:00pm


OSTERVILLE PACKAGE STORE 11 Wianno Ave,(508) 428-6327

We are proud of our selection of wines - from vineyards all over the world!  Beers- domestic, imported, non-alcoholic and micro-brew.  Liquors and liqueurs - the usual and unusual brands.  We also carry sodas, mixers, ice and bar supplies.  Come browse. 

Hours: Monday-Thursday 9:00am - 7:00pm; Friday & Saturday 9:00am -8:00pm; Closed on Sunday


OSTERVILLE HOUSE & GARDEN, 846 Main Street(508) 428-6911

A convenient hardware store, with everything for the home, garden, and more. Now carrying Benjamin Moore Paint! 

Other brands include: Weber, Big Green Egg, Yeti Coolers, Colonial Candle, Scotts and much more. 

Hours: Mon-Fri 7:30am- 5:30pm, Sat 8:00am-5:30pm, Sun 10:00am-4:00pm



DEPRISCO JEWELERS, 32 Wianno Ave.(508) 420-7400

DePrisco jewelers since 1948; offering the absolute finest quality jewelry at the fairest below retail price. DePrisco also makes one-of-a-kind pieced from the world's most renowned jewelry designers. Our staff is dedicated to providing personalized service. For decades, New England's families have trusted DePrisco to be their personal jeweler.

Hours: Monday thru Saturday 10:00-5:00pm


SILVA JEWELERS, 1112 Main Street(888) 222-2717

Silva Jewelers is a family owned fine jewelry and gift store located within the seaside village of Osterville in Massachusetts. We have been servicing our clientele for over 30 years. Silva Jewelers specializes in custom hand crafted jewelry items. We pride ourselves in our detail oriented customer service. We offer an Estate Jewelry consignment and brokerage service utilized by our customer base throughout New England. When you deal with Silva Jewelers, you deal with the owners.

Hours: Monday thru Saturday 10:00-5:00pm



CHECKERBERRY HOUSE INTERIORS, 857 Main St. (508) 428-5533

Looking for house warming, hostess gift, or something unique? From picture frames to rugs, you will find what you need at CHI. Checkerberry House Interiors has been offering personal service in decorating homes since 1969. We are a full service design center and offer window treatment, custom carpeting, upholstering, slipcovers, lamps and furniture. We also have 2,500 fabrics and wallpapers to select from. We are also a priority dealer fro Hunter Douglas. In addition  we have offer 1000 accessories and gifts in our retail shop.


COASTAL STYLE, 846 Main Street(508) 317-8689

Furniture and Gifts and accessories that are seaside inspired. Coastal Style has something for everyone.


OAK & IVORY, 1112 Main Street (508) 428-9425

We provide a wide assortment of gifts primarily with a coastal or nautical theme. Many of our products are hand made for us exclusively and therefore not always in stock. We also have available custom made items that you can choose from. These items represent a small portion of our large selection of merchandise.

Hours: Monday-Saturday 10:00am-5:00pm, Sunday 12-4:00pm


OYSTER ISLAND EMPORIUM, 846 Main Street(508) 428-5050

We  offer an extensive selection of Vera Bradley handbags, accessories, luggage and limited edition items. Also, Vera Bradley products including stationery, tableware, home accessories, rugs and easy rolling luggage. Plus, American crafts, lamps, door knockers, ship models, weather instruments, Nantucket style baskets, glass, pottery, collectibles, baby and bath products.  Choose practical, functional or whimsical OIE has it all!Need Invitations for amn upcoming event? OIE has a large selection.

Hours: Monday through Saturday 10:00am-5:00pm, Sunday 11am-4:00pm



Whether you’re looking for coffee & conversation, take-out, or a delicious dinner, you will find it in Osterville!


AMIE BAKERY, 1254 Main Street(508) 428-1005

Sunday-Monday 8:00am - 1:00pm, Tuesday - Saturday 7:00am-3:00pm

We also put a lot of care into what we feed our customers. At Amie we make everything from scratch and in small batches. We use local ingredients from artisans who, like us, are passionate about what they do. From traditional pastries and classic breakfast and lunch items to homemade sodas and ice cream floats—we serve up food people love, in a place no one wants to leave.



Carol Williams Catering offers personal service that will ensure your event to be imaginative and exciting.

Dependability and consistency are assured by our well-trained staff.

Carol Williams is a Certified Executive Chef as designated by The American Culinary Federation. 


CHART ROOM AT CROSBY'S, 330A West Bay Road (774) 602-8156

Opening Spring 2017


Couto Management Group provides top quality multi-brand restaurant operations that deliver superior customer service. Our aim is to provide our customers a great place to enjoy the products of the brands that we serve; to deliver outstanding business results to our shareholders; and, to provide our employees with a best in class organization that encourages professional growth and development.

Our goal for each guest transaction is to deliver quality products in clean restaurants, served by fast and friendly team members.


CREATIVE CLAMBAKES | (508) 843-2759

Homemade New England clam “chowdah”, appetizers, or a raw bar including shrimp cocktail, oysters on the half, and cherry stones.  We also offer marinated chicken and beef tips.  Whatever fits your needs.

Want something different?  How about having a Pig Roast or a barbeque. The same great service is available.  Benefits also include all paper products, lobster crackers, and clean up.

We also have tables and chairs for rent so you have everything you need from one business. For more information call or email us for your creative clambake, pig roast, or barbeque.



Crisp Flatbread Inc serves fresh wood-fired pizza and homemade pastas prepared with seasonal, local ingredients. We support local farmers, and are passionate about using hormone and nitrate-free meats and organic vegetables whenever possible. All of our pastas, sauces and CRISP flatbread dough are made from scratch with love.



Breakfast and Lunch - Natural Foods to Go!

Earthly Delights offers a wide selection of natural foods, and has something for everyone's specific dietary concerns, including many organic, vegetarian, and vegan selections.

Hours: Monday-Friday 7:00am-4:00pm, Saturday 8:00am-3:00pm

In-season: Sundays open 8:00am-2:00pm days.


FIVE BAY'S BISTRO, 825 MAIN STREET(508) 420-5559

Located in the heart of one of the most picturesque villages on Cape Cod, Five Bays Bistro offers modern yet classic food and atmosphere worthy of a major city. The Bistro serves award winning contemporary new American cuisine, with a more casual small plates menu at the bar.

Executive Chef Tim Souza has over 30 years of experience in the restaurant industry, and is a graduate of the Culinary Institute of America. He and General Manager Jamie Surprenant strive to offer an innovative menu that takes full advantage of fresh local ingredients, together with a carefully selected wine list to complement each dish.

Hours: Mon-Sun 5:00 pm-10:00 pm





​Wimpy's restaurant offers an extensive menu that's great for the whole family. Our three distinct dining rooms will please everyone. Wimpy's market has the freshest fish as well as desserts, soups, prepared foods and our award winning Quahog chowder. Our entire menu is also available for take-out through the market.

Hours: Mon-Sat 11:30am - Close, Sunday Brunch 11:00am- 2:00pm, Dinner till close.