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15-August-2025 Local Adventures & Superhost Shawn’s Travels
There’s something special about sipping a crisp Chardonnay or a hoppy local IPA with the breeze off the Chesapeake Bay brushing your cheek. One of my favorite ways to ease into vacation mode is to spend a slow afternoon exploring the local wineries and tucked-away breweries near Deale.
These spots aren’t about crowds or flash—they’re about character, connection, and savoring the moment. Whether you're visiting for a retreat at Chesapeake Paradise or simply in need of a laid-back coastal escape, these hand-picked gems offer the perfect pairing for presence, pleasure, and peaceful fun.
Nestled on a historic farmstead just inland, Thanksgiving Farm feels like stepping into a secret garden of small-batch excellence. The estate-grown red blends and airy patio make it ideal for slow sips and deep conversations. They offer weekend tastings and often feature local charcuterie or small bites for pairing. Reservations are recommended for groups.
This boutique winery is both elegant and earthy, known for sustainable practices and gorgeous rolling vines. The tasting room is modern and sleek, but it’s the outdoor seating that steals the show. Dodon’s private tastings include generous pours and detailed stories behind each bottle—perfect for a deeper connection to the land and the process.
Fridays Creek is housed in a beautifully restored tobacco barn that doubles as an art gallery. Their cozy tasting room serves up creative, small-batch wines in a relaxed setting. It’s a low-key spot perfect for chatting with locals, enjoying local artwork, and grabbing a bottle to bring back to enjoy on the lawn at CP.
A rustic vineyard tucked just outside downtown Annapolis, Great Frogs offers tastings in a cozy barn surrounded by rows of grapes. Known for their Meritage blends and scenic charm, it’s an ideal stop for couples or small groups looking for something intimate and authentic. Perfect for picking up a bottle to open during golden hour on the Chesapeake Paradise balcony.
Forward Brewing is a small, community-driven brewery located just off the beaten path in Eastport. Their rotating tap list includes creative sours, hazy IPAs, and crisp pilsners. The vibe is casual, with seating spilling into a converted garage and shady outdoor patio. It’s a favorite for both locals and day-trippers.
A classic Maryland brewery with award-winning IPAs, dark ales, and seasonal favorites. The taproom is welcoming and the beer is fresh—great for a relaxed afternoon stop before heading back to Chesapeake Paradise with a growler in hand.
A hidden gem for beer lovers who appreciate small-batch experimentation. Known for their cask ales and English styles, this laid-back taproom offers board games, community events, and a friendly, down-to-earth vibe.
Part garden center, part taproom, The Beer Farm is a charming little spot serving local craft brews inside one of the area's most beloved nurseries. Casual, dog-friendly, and quirky in the best way—pick out a plant and a pint before heading home to sip on the balcony or under the stars at CP.
Midday tastings (especially between 1:00 PM and 4:00 PM) tend to strike the perfect balance:
Fewer crowds, more ambiance
Ideal lighting and weather
More attentive service
If you’re staying at Chesapeake Paradise, it also leaves you plenty of time to come home, relax in the hot tub, and catch the sunset over the bay.
Many of these hidden gems are small and may only have a handful of indoor tables or limited outdoor seating. If you’re traveling with others:
Reserve a table or tasting experience
Ask about food, pet, or group policies
Plan transportation or ride-share option
Mix & Match with Food
Wineries
Thanksgiving Farm often offers cheese boards or allows outside picnic food (call ahead).
Dodon offers curated food pairings during events or by request.
Great Frogs sometimes has live music and food trucks during special events.
Breweries
Forward Brewing has a seasonal pub menu that pairs well with rotating beers.
Mully’s Brewery in Prince Frederick frequently hosts food trucks during weekends, creating a vibrant, sociable atmosphere.
Chesepiooc allows outside food or orders from nearby spots—perfect for games and grazing.
The Beer Farm at Homestead Gardens offers small-batch craft brews in a lush garden setting, often accompanied by live music and a relaxed, family-friendly vibe.
Tip: Keep a small cooler with water, crackers, or fruit to stay grounded between sips.
It can be tempting to visit all the places in one afternoon, but the magic lies in lingering:
Choose two stops for a half-day outing
Give yourself time to savor conversations, scenery, or strolls
One good experience is often more memorable than three rushed ones
Guests often grab a bottle or crowler to enjoy back at the property:
Ask about seasonal or limited-edition offerings
Many offer discounts on multi-bottle purchases
Having a special bottle for sunset by the water is a guest favorite
A retreat isn’t just about what happens on the property—it’s about how your entire experience invites you to slow down, savor, and connect. Exploring the wine and craft beer scene near the bay gives guests a chance to:
Enjoy the flavors and artistry of local makers
Spend quality time with friends or colleagues
Relax in a grounded, meaningful way
These spots mirror what Chesapeake Paradise is all about: simple luxuries, nature-inspired connection, and spaces that let you exhale.
Whether you're a wine devotee or a curious beer taster, the Deale area offers more than just a buzz—it offers a chance to experience the rhythm of local life. And after a day of laughter, flavor, and discovery, you’ll come back to Chesapeake Paradise with a full heart (and maybe a bottle or two for sunset by the water).
You could be sipping a chilled rosé or a hazy IPA by the water this weekend if you book now. [Check out our accommodations and book here.]