Your Guide to Fall Shopping in Gloucester, MA

August 20, 2025 / Things to Do & See

Gloucester is the perfect destination for a fall getaway — and there’s no better time to refresh your wardrobe, update your home, and stock up on seasonal flavors from local shops. Whether you’re looking for cozy layers, autumn-inspired homegoods, or ingredients for your favorite fall recipes, Gloucester offers a variety of shopping spots that blend local charm with practical finds.

Update Your Fall Wardrobe at Second Glance Thrift Store

Fall in Gloucester calls for soft sweaters, cozy scarves, and warm layers, and you’ll find plenty of options at Second Glance Thrift Store. This local favorite offers gently used clothing and accessories at great prices, making it easy to refresh your wardrobe sustainably. From transitional pieces for early fall to heavier coats for the chillier months, Second Glance is a go-to stop for shoppers who love unique finds with plenty of character.

Find the Perfect Fall Shoes at Mark Adrian Shoes

Once you’ve picked out your autumn wardrobe, head to Mark Adrian Shoes to complete the look. This longstanding Gloucester business specializes in helping customers find the right fit, now enhanced by their cutting-edge 3D scanning technology. Whether you’re shopping for stylish boots, comfortable sneakers, or practical shoes for everyday wear, Mark Adrian Shoes has options that balance style and comfort — perfect for exploring Cape Ann this fall.

Refresh Your Home for the Season at goodlinens studio

Fall is the season of cozy living, and goodlinens studio is the perfect place to give your home a seasonal refresh. Located in downtown Gloucester, goodlinens carries thoughtfully designed kitchen and homegoods that are as practical as they are beautiful. Stock up on quality linens, kitchenware, and décor to bring a touch of warmth and elegance to your space this autumn.

Add Seasonal Flavors from Cape Ann Olive Oil

No fall kitchen is complete without rich, flavorful oils and balsamics, and Cape Ann Olive Oil has you covered. Their seasonal selections — think pumpkin spice balsamic, cranberry pear balsamic, or robust, peppery olive oils — are perfect for creating fall-inspired salads, marinades, and roasted vegetable dishes. Stop by the tasting bar to sample unique combinations and bring home flavors that make autumn cooking even better.

Shop for Fall Recipes at Common Crow Natural Market

For fresh, local ingredients to pair with your seasonal cooking, visit Common Crow Natural Market. This Gloucester staple offers organic produce, bulk pantry items, and specialty products that make it easy to prepare nourishing fall recipes. Whether you’re planning a cozy night in with homemade soup or gathering ingredients for your favorite baked goods, Common Crow is a great stop for anyone who loves healthy, flavorful food.

Shop, Sip, and Dine at Beauport Boutique

While you’re exploring Gloucester’s waterfront, don’t miss the Beauport Boutique inside the Beauport Hotel. The boutique features curated gifts, clothing, and accessories, perfect for treating yourself or finding something special to take home. While you’re there, make a day of it by grabbing a drink at the bar or enjoying lunch or dinner at 1606 Restaurant & Oyster Bar — a perfect way to round out a fall shopping trip.

Plan Your Fall Getaway to Gloucester

Shopping is just one reason to visit Gloucester this fall. From scenic coastal walks to seasonal events and local dining, there’s so much to enjoy during the cooler months. Start planning your fall trip and discover more things to do, places to stay, and events to explore here.