Westport, Conn., is known for its charming downtown area filled with boutique shops, high-end retailers, and unique finds. For those who enjoy shopping in Westport, CT, the town provides a diverse mix of local shops, designer boutiques, and antique stores, making it ideal for both casual and serious shoppers. Whether you’re looking for clothing, home decor, or one-of-a-kind gifts, Westport has something to offer everyone.
This guide will introduce you to some of the best places to shop in Westport, giving you an insider’s look at where to find quality items and enjoy the town's vibrant shopping scene.
Westport Farmers’ Market
The Westport Farmers’ Market is more than just a place to shop — it’s a vibrant community hub centered around fresh, local, and sustainably grown food. Open year-round, the market brings together farmers, artisans, and food lovers at two convenient locations: outdoors on Imperial Avenue in the warmer months and indoors across the Saugatuck River during winter and spring. From organic produce and small-batch baked goods to handmade crafts and gourmet specialties, the market offers a wide variety of high-quality, locally sourced products. With a welcoming atmosphere and a mission rooted in health, education, and sustainability, it’s a must-visit for anyone looking to support local makers and enjoy a more mindful shopping experience.
Terrain
Terrain, located on the Post Road in Westport, is a beautiful garden store and home goods retailer that brings nature-inspired beauty to your home. Specializing in plants, outdoor furniture, and gardening tools, Terrain offers a wide range of products to help you create a serene and stylish environment in your home and garden. The store also features a variety of home decor items, including candles, vases, and artwork that complement its botanical themes. The store’s peaceful atmosphere and thoughtfully designed displays make it a pleasant place to browse and find the perfect item for your home or garden.
Design Within Reach
Design Within Reach is a must-visit for anyone drawn to contemporary and modern furniture. From sleek sofas and sculptural chairs to minimalist lighting and sophisticated accessories, the store’s curated collection blends thoughtful design with everyday practicality. Emphasizing clean lines, modern aesthetics, and high-quality materials, each piece is crafted to elevate your living space with timeless appeal. The knowledgeable staff is always ready to help you find just the right piece to suit your style and needs, making the shopping experience as seamless as it is inspiring.
Anthropologie
Housed in the beautifully restored 1924 Bedford Mansion and former Westport Firehouse and Westport YMCA, Anthropologie brings its signature eclectic style to the heart of Bedford Square. This national retail favorite is anything but ordinary in Westport — its historic setting adds architectural charm to the brand’s already captivating shopping experience. Known for its bohemian-inspired fashion, home décor, and accessories, Anthropologie offers a thoughtfully curated mix of textures, prints, and colors that feel both whimsical and refined. From statement dresses and cozy sweaters to unique furniture, wall art, and scented candles, the store invites visitors to explore every corner. Whether you're updating your wardrobe or refreshing your living space, Anthropologie is a must-visit for creative inspiration in a truly iconic setting.
Bungalow
Step into Bungalow and you’ll quickly understand why it was named the most beautiful store in Connecticut by Architectural Digest. Curated by founder Wende Cohen, this one-of-a-kind lifestyle boutique in downtown Westport is a destination for interior designers, celebrities, and tastemakers from around the globe. Blending timeless elegance with worldly charm, Bungalow features an exquisite mix of furniture, fine jewelry, gifts, and home accessories—each piece hand-selected for its beauty, character, and sense of place. Wende’s discerning eye and serene, layered aesthetic have shaped the shop’s signature style, where age and imperfection are celebrated. More than a store, Bungalow is a source of inspiration for those seeking elevated, soulful design.
Winged Monkey
Winged Monkey is a beloved Westport boutique offering a thoughtfully curated selection of clothing, shoes, and accessories for women and girls. Best known for its standout collection of special occasion dresses and gowns, it’s a go-to destination for prom, weddings, and any event where style matters. Beyond formalwear, you’ll also find casual, everyday pieces that reflect a fresh, fashion-forward sensibility. As a locally owned small business, Winged Monkey prides itself on personalized service—helping customers find the perfect fit, style, or accessory with a friendly, hands-on approach. Whether you're shopping for a major event or just updating your wardrobe, Winged Monkey delivers a truly one-on-one boutique experience.
Catherine H
Since opening in 2008, Catherine H has become a go-to boutique in Westport for women seeking casual-chic style with a timeless twist. Owner Catherine Byn curates each season’s collection with care, selecting ethically made pieces from designers who prioritize quality, fit, and wearability. The boutique is known for clothing that’s soft, flattering, and classic—yet never boring. With a focus on building lasting wardrobes rather than fleeting trends, Catherine H offers a warm, personalized shopping experience that helps women feel confident and at ease. Whether you're looking for everyday staples or elevated essentials, Catherine H delivers style that feels as good as it looks.
South Moon Under
South Moon Under brings effortless style to downtown Westport with its curated collection of women’s apparel, swimwear, shoes, accessories, and home décor. Blending trendy with timeless, the boutique offers something for every occasion—whether you’re heading to the beach, brunch, or a night out. Known for its accessible price points and fashion-forward finds, South Moon Under is a favorite among shoppers looking to refresh their wardrobe with pieces that are both versatile and stylish. With new arrivals each season, it’s the perfect spot to discover your next go-to look.
Sundance Catalog
Founded by Robert Redford in 1989, Sundance Catalog brings an artful, soulful sensibility to Westport’s shopping scene. This thoughtfully curated boutique features a distinctive blend of women’s apparel, handcrafted jewelry, artisan accessories, and one-of-a-kind home décor. Every item reflects a commitment to quality, craftsmanship, and individuality—perfect for shoppers who appreciate style with substance. With its blend of Western-inspired elegance and artistic flair, Sundance offers a shopping experience that feels personal, inspiring, and refreshingly unique.
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Reach out today and experience the difference of working with Riverside Realty Group.
