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Learn More About the Eastern Shore of Maryland and Chesapeake Bay

Sandaway Suites & Beach Blog for Traveling to Oxford, Maryland

Helpful advice and information for planning a Maryland vacation is found in our travel blog. Discover why Sandaway Suites & Beach has an ideal location for exploring the Eastern Shore and Chesapeake Bay. 

Sandaway Suites & Beach Blog - Travel Tips and Advice for Eastern Shore of Maryland Vacations

<h1 data-path-to-node="12">Sip, Stay, and Savor: The 2026 Guide to Maryland Wine Festivals</h1>
<p data-path-to-node="14">There is a specific kind of magic that happens when the Chesapeake breeze meets a crisp glass of Maryland Chardonnay. Here at <strong data-path-to-node="14" data-index-in-node="126">Sandaway Suites &amp; Beach</strong>, we are lucky enough to have a front-row seat to one of the most anticipated events on the East Coast: <strong data-path-to-node="14" data-index-in-node="253">WineFest at St. Michaels.</strong></p>
<p data-path-to-node="15">As we celebrate Maryland Wine Month this March, it&rsquo;s the perfect time to plan your cork-popping getaway. From our historic "town-wide" tasting in April to the harvest festivals of autumn, here is your definitive guide to the 2026 Maryland wine season.</p>
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<h2 data-path-to-node="17">The Main Event: WineFest at St. Michaels 2026</h2>
<p data-path-to-node="18"><strong data-path-to-node="18" data-index-in-node="0">Dates: April 25 &ndash; 26, 2026 | 11:00 AM &ndash; 5:00 PM</strong></p>
<p data-path-to-node="19">Imagine the entire town of St. Michaels transforming into a giant, walkable tasting room. Instead of being confined to a single field, you&rsquo;ll stroll through our historic streets, ducking into luxury inns, waterfront courtyards, and local restaurants to sample over <strong data-path-to-node="19" data-index-in-node="265">250 world-class wines</strong>.</p>
<h3 data-path-to-node="20">What&rsquo;s New for 2026?</h3>
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<p data-path-to-node="21,0,0"><strong data-path-to-node="21,0,0" data-index-in-node="0">Friday Night Kickoff:</strong> Don't miss "Wines from George&rsquo;s Cellar" on April 24th, featuring rare 20-year-old vintages from the festival founder's private collection.</p>
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<p data-path-to-node="21,1,0"><strong data-path-to-node="21,1,0" data-index-in-node="0">The VIP Upgrade:</strong> Hosted at the Old Brick Inn, the 2026 VIP pass includes seated masterclasses focusing on 90+ point wines from legendary regions like Bordeaux and Napa.</p>
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<p data-path-to-node="21,2,0"><strong data-path-to-node="5,0" data-index-in-node="0">The Sandaway Advantage:</strong> Staying with us in Oxford offers the best of both worlds. We are located just one block from the historic <strong data-path-to-node="5,0" data-index-in-node="130">Oxford-Bellevue Ferry</strong>&mdash;your 10-minute "shortcut" across the Tred Avon River. After the scenic crossing, you're just a short, pleasant drive into St. Michaels. You get to enjoy the festival energy during the day and retreat to the quiet, waterfront charm of Oxford for the sunset.</p>
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<p data-path-to-node="22"><strong data-path-to-node="22" data-index-in-node="0"><a class="ng-star-inserted" href="https://www.winefestatstmichaels.com/" target="_blank" rel="noopener" data-hveid="0" data-ved="0CAAQ_4QMahgKEwjGv5Sn56KTAxUAAAAAHQAAAAAQlQE">Click Here to Purchase WineFest 2026 Tickets</a></strong></p>
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<h2 data-path-to-node="24">Safety First: Navigating Your Wine Tour Responsibly</h2>
<p data-path-to-node="25">We want your 2026 wine season to be memorable for all the right reasons. Whether you are staying in town or traveling from nearby, here is how to enjoy the festivals responsibly:</p>
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<p data-path-to-node="26,0,0"><strong data-path-to-node="26,0,0" data-index-in-node="0">The Designated Driver (DD) Ticket:</strong> Almost every major festival, including St. Michaels, offers a discounted DD ticket (usually <strong data-path-to-node="26,0,0" data-index-in-node="127">$20&ndash;$25</strong>). These tickets include a souvenir glass for non-alcoholic drinks and free water/soda.</p>
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<p data-path-to-node="26,1,0"><strong data-path-to-node="26,1,0" data-index-in-node="0">Rideshare &amp; Taxis:</strong> Uber and Lyft are available in Talbot County, but demand is extremely high during WineFest. We recommend using <strong data-path-to-node="26,1,0" data-index-in-node="130">Uber Reserve</strong> to schedule your ride 24 hours in advance.</p>
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<p data-path-to-node="26,2,0"><strong data-path-to-node="26,2,0" data-index-in-node="0">Local Car Services:</strong> For a guaranteed ride, book a local service like <strong>Bay Country Taxi</strong>&nbsp;or <strong>Scotty's&nbsp;Taxi Service</strong> for your group.</p>
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<p data-path-to-node="26,3,0"><strong data-path-to-node="26,3,0" data-index-in-node="0">Arrival by Sea:</strong> The <strong data-path-to-node="26,3,0" data-index-in-node="20">Watermark Cruise from Annapolis</strong> offers a round-trip voyage directly to St. Michaels on April 25th&mdash;perfect for those who want to let a professional Captain handle the navigation!</p>
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<h2 data-path-to-node="28">2026 Maryland Wine Festival Calendar</h2>
<h3 data-path-to-node="29">1. A Maryland Wine Experience (Frederick)</h3>
<p data-path-to-node="30"><strong data-path-to-node="30" data-index-in-node="0">Dates: March 20 &ndash; 22, 2026</strong> The perfect way to celebrate Maryland Wine Month! This boutique event features Master Classes with winemakers and a Grand Tasting in downtown Frederick.</p>
<h3 data-path-to-node="31">2. Wine in the Woods (Columbia)</h3>
<p data-path-to-node="32"><strong data-path-to-node="32" data-index-in-node="0">Dates: May 16 &ndash; 17, 2026</strong> A high-energy weekend in Symphony Woods featuring live bands and dozens of Maryland wineries.</p>
<h3 data-path-to-node="33">3. The Maryland Wine Festival (Westminster)</h3>
<p data-path-to-node="34"><strong data-path-to-node="34" data-index-in-node="0">DATE CHANGE: Saturday, June 6, 2026</strong> <strong data-path-to-node="34" data-index-in-node="36">Note:</strong> For the first time in 42 years, this legendary festival has moved from September to <strong data-path-to-node="34" data-index-in-node="126">June</strong>! This "Sip into Summer" celebration at the Carroll County Farm Museum now features a strong focus on seafood pairings.</p>
<h3 data-path-to-node="33">4.&nbsp;Autumn Wine Festival (Salisbury)</h3>
<p data-path-to-node="34"><strong data-path-to-node="8,0" data-index-in-node="36">Dates: October 17&ndash;18, 2026</strong> Held at Pemberton Historical Park, this is the perfect way to wrap up the season with regional food, live music, and the first crisp air of autumn on the Eastern Shore.</p>
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<p data-path-to-node="8,0">&nbsp;</p>
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<h2 data-path-to-node="36">Pro-Tips for Your 2026 Wine Tour</h2>
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<p data-path-to-node="37,0,0"><strong data-path-to-node="37,0,0" data-index-in-node="0">Book Your Room Early:</strong> WineFest weekends are our busiest of the year. <a class="ng-star-inserted" href="https://www.sandaway.com" target="_blank" rel="noopener" data-hveid="0" data-ved="0CAAQ_4QMahgKEwjGv5Sn56KTAxUAAAAAHQAAAAAQlgE">Check our 2026 availability at Sandaway here.</a></p>
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<p data-path-to-node="37,1,0"><strong data-path-to-node="37,1,0" data-index-in-node="0">The 2-Day Strategy:</strong> Buy the 2-Day General Admission pass. Use Saturday to scope out your favorite wineries and Sunday (which is typically less crowded) for deeper tastings and retail shopping.</p>
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<p data-path-to-node="37,2,0"><strong data-path-to-node="37,2,0" data-index-in-node="0">The "Wine Wardrobe":</strong> April on the Eastern Shore is beautiful but unpredictable. Wear comfortable, closed-toe walking shoes and bring a light layer for the evening breeze.</p>
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<h3 data-path-to-node="38">Ready to Sip and Stay?</h3>
<p data-path-to-node="39">We would love to host you for a weekend of relaxation and discovery. See you on the waterfront!</p>

Maryland Wine Festivals & St. Michaels Guide 

Discover the best of Maryland’s viticulture this season with our comprehensive guide to the 2026 wine festival circuit. From the world-class "town-wide" tasting at WineFest at St. Michaels to the newly rescheduled summer dates for the Maryland Wine Festival, we’ve rounded up the must-attend events, essential safety and transportation tips, and pro-advice for making the most of your stay on the Eastern Shore. Whether you’re planning a romantic waterfront getaway or a weekend of discovery with friends, here is everything you need to sip, stay, and savor the finest local pours this year.

Plan your 2026 Maryland wine tour! From WineFest at St. Michaels to safety tips & designated drivers—stay at Sandaway Suites & Beach for the ultimate getaway.

wine festivals