Escape to Gloucester Main Street Village for an unforgettable girlfriend's getaway weekend! Nestled near the historic towns of Williamsburg, Yorktown, and Jamestown, Gloucester Main Street is a hidden gem with deep colonial roots and vibrant contemporary charm. Stroll through this lively village where Revolutionary War patriots once mustered on the courthouse steps, indulge in rich cultural experiences, savor incredible cuisine, and explore a myriad of unique shopping options. From the perfect morning coffee spot to a cozy nightcap venue, Gloucester Main Street offers everything you need for a relaxing and fun-filled weekend with your best friends. Discover why this historic village is the ultimate destination for your next girlfriend's getaway!

STAY

Stay in The Loft on Main Street, a completely renovated condo located right in the heart of Historic Gloucester Main Street. This charming condo is just steps away from everything Main Street has to offer. Access Main Street through a picturesque cobblestone alleyway, and be sure to spend some time outside on the second-story balcony, which overlooks a beautifully landscaped courtyard below.

Also consider: The Inn at Warner Hall, Holiday Inn Express - Gloucester, Hampton Inn - Gloucester, and Airbnb listings in the heart of Main Street like Bee Goode House, a Bitt of Home, and the Blue Crab.

BRUNCH

Sweet Tooth Café. Start your morning on Gloucester Main Street with a visit to Sweet Tooth Café. Treat yourself to a gourmet coffee or a flavorful latte from their diverse selection. Sweet Tooth isn't just a coffee shop—it's a full bakery and café offering an expansive menu that includes everything from tasty breakfast options to delectable sweets. Whether you're in the mood for a leisurely brunch or a quick pick-me-up, Sweet Tooth caters to all tastes, including vegetarian, gluten-free, low-carb, and healthy choices. Take your time enjoying the cozy ambiance as you plan your day ahead with your friends.

LUNCH

Patriots Grill. A must-visit on Gloucester’s Main Street. Patriots Grill offers a laid-back lunch experience with delicious American-style cuisine. Indulge in their themed dishes such as the “Freedom Philly,” the “All American” burger, and “The Jamestown.” Plus, they’re open for dinner, making it an ideal spot to immerse yourself in American history and venture a little further into Gloucester Main Street.

Olivia's in the Village. a beloved Gloucester staple renowned for its family-centered, family-style dining experience. With years of community presence, Olivia’s offers a welcoming atmosphere and a diverse menu. Olivia’s is a family centered, family style eatery, open for breakfast, lunch, and dinner.

Also consider: Wondering Gypzs Kitchen

AFTERNOON DRINKS

Gloucester Brewing Company. Enjoy an afternoon beer at Gloucester Brewing Company, Gloucester’s premier hometown microbrewery. Located conveniently on the corner of Main Street, it's within walking distance of all the vibrant restaurants and shops. Their menu boasts a variety of ales, IPAs, stouts, pilsners, and seltzers to suit every palate. Gloucester Brewing Co. is not just a brewery; it's a lively venue hosting musicians, trivia nights, and a rotating lineup of food trucks. Don’t miss their rooftop seating, offering an impressive view of Main Street!

Kelsick Specialty Market. For another delightful afternoon option, visit Kelsick Specialty Market, an ideal spot for gourmet lovers! Head to Kelsick, order a charcuterie board and pick out a bottle of wine from their extensive selection. The market is a wonderful place to find specialty foods, drinks, and even unique gifts. Situated right in the heart of Main Street, Kelsick is the perfect place to stop for a quick drink before heading to dinner!

DINNER

Lulu Birds Kitchen. Find Lulu Birds Kitchen for a dinner of elevated Southern comfort foods. With reimagined traditional dishes and delicious drinks, Lulu Birds is an unforgettable restaurant experience. The ambiance of Lulu Birds only adds to the experience, providing a high-class, yet comforting atmosphere, a perfect match to their elevated comfort foods.

Also consider: Farmasea, Bangkok Noi Thai Cuisine

SHOP

Main Street is home to boutiques, antique shops, a produce market, and many other small businesses. At The Silver Box, it's all about women’s jewelry, clothing, accessories, and gifts! Swing by Up South to explore more women’s fashion, featuring fabulous jewelry brands like Enewton and other must-have labels. And don't forget to step into Yolanda's, where the spotlight shines on women’s clothing, accessories, and the perfect pair of shoes to complete your look! Ware Neck Produce, established in 1985, offers fresh local fruits, vegetables, seafood, canned goods, and flowers. Grab a quick and easy snack at Northern Neck Popcorn Bag—they have so many delicious flavors it will be hard to choose just one! Looking for the perfect jewelry? Head over to Vashti's Jewelers. They have a stunning array of jewelry that caters to every style and occasion. Step into a world of an unparalleled collection of antiques at Goodman's Antiques & Estate Jewelry! Experience heartfelt service and stunning flowers at Smith's Florist & Gift Shoppe. Whether it's a special occasion or just because, they offer the perfect blooms to brighten your day, along with a variety of thoughtful gifts.

EXPLORE

For the History Lover:

History lovers will find much to explore in Gloucester’s Historic Courthouse Circle, which serves as Gloucester’s Visitor Center and a gateway to the past. The Historic Courthouse Circle is home to five buildings: the debtors' prison, the jail, the Roane Building, the Clayton Building, the courthouse, and one Confederate monument. Remarkably, the court circle has remained relatively unchanged since the 18th century.

A must-visit is the Gloucester Museum of History. Formerly known as the Botetourt Building, this historic structure was built in 1770 and originally served as a tavern for travelers heading to Gloucester Courthouse. Today, the museum houses over 3,000 objects, ranging from archival documents and photographs to antique agricultural tools.

Not only can history buffs explore the past, but they can also immerse themselves in it by taking a class or a tour at The Village Blacksmith. The Village Blacksmith offers scheduled classes and tours almost every weekend. Begin your journey into the art of metalworking with an experience led by George Cramer. There's no better place to explore history than at The Village Blacksmith.

For the Art Enthusiasts:

Art enthusiasts will love Gloucester's Main Street! This vibrant area boasts an impressive collection of art galleries, a museum, murals, and statues for the public to enjoy. Walking down Main Street, you'll find several notable galleries:

Gloucester Arts on Main: A non-profit organization housing a gallery for artists to exhibit their work and offering workshops, classes, and various events.
York & Main: A showroom, shop, and artist studio hosting monthly events and pop-ups featuring regional creatives.
Village Art Colony: A gallery showcasing local artists' work.

The Fine Arts Museum of Gloucester offers a dynamic range of visual arts, including paintings, sculptures, and multimedia installations, with a rotating collection that continually brings fresh perspectives to the community. It also serves as the home base for the Cook Foundation, a non-profit organization established in 1999 with a mission to support and promote the arts in Gloucester, Virginia. As part of this mission, the Cook Foundation has contributed six stunning murals and numerous public art exhibitions along Main Street, enriching the town's cultural landscape and providing artistic enjoyment for all residents and visitors.

Art lovers can enjoy perusing the galleries and the Fine Arts Museum of Gloucester, while also admiring the six colorful murals adorning the facades of buildings along Main Street.

For the Self-Care Devotees:

Self-care devotees will find plenty to enjoy on Gloucester’s Main Street!

The area is brimming with hair salons, including Hair on Main, LC Salon, and Split Enz Salon. Split Enz offers a variety of services, and you can even book a spa package for a more in depth self-care experience!

There are numerous wellness businesses, including Heart Felt Touch Massage Therapy and The Nurtury where the focus is on treatments and events designed to help people relax and improve their overall well-being. From soothing massages to acupuncture sessions and holistic wellness programs, you'll find a range of options to rejuvenate your mind and body.

Main Street also features Mariposa Medical Spa, a medical spa offering advanced, medical-grade treatments for enhancing inner and outer beauty, wellness, and complete revitalization. If you're feeling tired from your girlfriends' getaway, book an appointment at Mariposa Medical Spa for the ultimate rejuvenation with IV hydration sessions that will refresh and energize you!

Whether you're seeking a new hairstyle, a relaxing massage, or a transformative wellness treatment, Main Street has everything you need to take care of yourself.

Also consider: Wellness House, Gate of Life Acupuncture