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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

<div>
<h2>Exploring Movie Magic: Legendary Films Shot on Maryland's Eastern Shore</h2>
<div>
<p class="editor-paragraph" dir="ltr">Step into the world of movie magic as we take a journey through Maryland's Eastern Shore, a legendary filming location that has played host to numerous iconic films throughout the years. From gripping dramas to heartwarming comedies, this picturesque region has provided the backdrop for some of Hollywood's most memorable moments.</p>
<p class="editor-paragraph" dir="ltr">Immerse yourself in the charm and beauty of this unique setting, as we delve into the stories behind these famous films. Discover how directors and producers were drawn to Maryland's Eastern Shore for its rustic appeal, stunning landscapes, and authentic atmosphere.</p>
<p class="editor-paragraph" dir="ltr">Uncover the secrets and behind-the-scenes anecdotes from the making of these legendary movies. Get a glimpse into the creative process that brought these stories to life on the silver screen.</p>
<p class="editor-paragraph" dir="ltr">Whether you're a film buff or simply curious about the movie-making process, this article is your backstage pass to the movie magic that has graced the shores of Maryland. So grab some popcorn, sit back, and join us as we explore the legendary films shot in this captivating coastal haven.</p>
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</div>
<div>
<h3>The History of Filmmaking on Maryland's Eastern Shore</h3>
<div>
<p class="editor-paragraph" dir="ltr">Maryland's Eastern Shore has a rich history of filmmaking, dating back to the early 20th century. It all began in the 1920s when the region's natural beauty caught the attention of filmmakers looking for unique locations. The Eastern Shore's rolling farmlands, picturesque waterfronts, and quaint small towns provided the perfect backdrop for period pieces and rural dramas.</p>
<p class="editor-paragraph" dir="ltr">One of the earliest films shot on the Eastern Shore was the silent film "The First Lady in the Land" (1929), which depicted the story of Martha Washington. This historical drama was shot in various locations throughout Talbot County, showcasing the region's colonial charm. The success of this film put Maryland's Eastern Shore on the map as a desirable filming location.</p>
<p class="editor-paragraph" dir="ltr">In the following decades, more filmmakers flocked to the Eastern Shore, attracted by its diverse landscapes and authentic atmosphere. The region became a favorite destination for directors and producers looking for a slice of Americana. As technology advanced and the film industry grew, Maryland's Eastern Shore continued to evolve as a prominent location for both Hollywood and independent productions.</p>
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<div>
<h3>Famous Films Shot in Talbot County MD</h3>
<div>
<p class="editor-paragraph" dir="ltr">Talbot County, located on Maryland's Eastern Shore, has been the setting for several well-known films that have left a lasting impact on audiences. These films range from romantic comedies to thought-provoking dramas, showcasing the versatility of the region's landscapes and architecture.</p>
<p class="editor-paragraph" dir="ltr">One of the most popular films shot in Talbot County is "Wedding Crashers" (2005), starring Owen Wilson and Vince Vaughn. This hilarious comedy follows two friends who crash weddings to meet women. The Eastern Shore's charming waterfront mansions and scenic coastal vistas provided the perfect backdrop for the film's wedding scenes. From the iconic St. Michaels wedding crash to the picturesque Chesapeake Bay boat scenes, the movie captured the essence of the Eastern Shore's beauty and charm.</p>
<p class="editor-paragraph" dir="ltr">Another notable film shot in Talbot County is "Failure to Launch" (2006), starring Matthew McConaughey and Sarah Jessica Parker. This romantic comedy tells the story of a man who still lives with his parents and the woman hired to make him move out. The film utilized various locations throughout the county, including historic Oxford, downtown Easton, and the stunning waterfront properties along the Miles River. The Eastern Shore's idyllic setting added to the film's romantic atmosphere, creating a visually appealing backdrop for the story.</p>
<p class="editor-paragraph" dir="ltr">In addition to these comedies, Talbot County has also been the setting for more serious films, such as "Clara's Heart" (1988), starring Whoopi Goldberg. This heartfelt drama tells the story of a Jamaican housekeeper who becomes a mother figure to a young boy. The film showcases the Eastern Shore's rural landscapes and small-town charm, providing a contrast to the bustling city life depicted in the story. Talbot County's rustic appeal added depth and authenticity to the film's narrative, making it a memorable cinematic experience.</p>
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<div>
<h3>The Unique Locations Used in These Films</h3>
<div>
<p class="editor-paragraph" dir="ltr">The films shot on the Eastern Shore of Maryland have utilized a wide range of unique locations, showcasing the region's diverse landscapes and historic architecture. From quaint small towns to sprawling waterfront estates, each film has taken advantage of the Eastern Shore's distinct charm.</p>
<p class="editor-paragraph" dir="ltr">In "Wedding Crashers," the filmmakers chose St. Michaels as the primary location for the wedding crash scenes. St. Michaels is a picturesque waterfront town known for its historic charm and stunning views of the Chesapeake Bay. The film's iconic wedding crash, where Owen Wilson's character jumps off a boat into a wedding reception, took place at the Chesapeake Bay Maritime Museum. This location provided a perfect backdrop for the film's comedic moments, showcasing the Eastern Shore's maritime heritage.</p>
<p class="editor-paragraph" dir="ltr">"Failure to Launch" utilized various locations throughout Talbot County to bring its story to life. The film's downtown scenes were shot in Easton, a vibrant small town with a historic district filled with charming shops and restaurants. The Miles River, which runs through Talbot County, served as the backdrop for the film's romantic boat scenes. The Eastern Shore's scenic waterways and lush landscapes added a touch of natural beauty to the film, enhancing its visual appeal.</p>
<p class="editor-paragraph" dir="ltr">In "Clara's Heart," the filmmakers captured the essence of the Eastern Shore's rural landscapes and small-town charm. The film utilized locations in Talbot County, such as Oxford and Easton, to depict the story's setting. Oxford, a quaint waterfront town known for its colonial architecture, provided a picturesque backdrop for the film's scenes. The Eastern Shore's slow-paced lifestyle and scenic beauty added depth to the film's narrative, creating a sense of authenticity and emotional resonance.</p>
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<div>
<h3>Impact of These Films on the Local Economy and Tourism</h3>
<div>
<p class="editor-paragraph" dir="ltr">The films shot on Maryland's Eastern Shore have had a significant impact on the local economy and tourism industry. These movies have brought national and international attention to the region, attracting visitors and boosting local businesses.</p>
<p class="editor-paragraph" dir="ltr">The success of films like "Wedding Crashers" and "Failure to Launch" put Talbot County on the map as a desirable tourist destination. Visitors from all over the country flocked to the Eastern Shore to experience the charm and beauty depicted in these films. The local economy benefited from increased tourism, with businesses such as hotels, restaurants, and shops experiencing a surge in visitors.</p>
<p class="editor-paragraph" dir="ltr">The films also provided job opportunities for local residents, as they often hired extras and crew members from the surrounding communities. This injection of employment opportunities helped stimulate the local economy and provided a boost to the region's workforce.</p>
<p class="editor-paragraph" dir="ltr">Additionally, the Eastern Shore's cinematic history has inspired the creation of film festivals and events that celebrate the region's connection to the movie industry. These events attract filmmakers, actors, and film enthusiasts from around the world, further promoting the Eastern Shore as a movie-making destination. The film festivals and events not only showcase the films shot in the area but also provide a platform for local filmmakers to showcase their work, fostering a vibrant creative community.</p>
</div>
</div>
<div>
<h3>Behind-the-Scenes Stories from the Film Sets</h3>
<div>
<p class="editor-paragraph" dir="ltr">Behind every legendary film shot on Maryland's Eastern Shore, there are fascinating behind-the-scenes stories and anecdotes that add depth to the movie-making process. These stories give us a glimpse into the challenges, creativity, and collaboration that goes into bringing a film to life.</p>
<p class="editor-paragraph" dir="ltr">During the filming of "Wedding Crashers," the cast and crew faced the unpredictable weather patterns of the Eastern Shore. The iconic wedding crash scene, which was shot outdoors, had to be rescheduled multiple times due to sudden storms. Despite the challenges, the team persevered and managed to capture the scene, resulting in one of the film's most memorable moments.</p>
<p class="editor-paragraph" dir="ltr">In "Failure to Launch," the filmmakers faced the unique challenge of shooting on the water. The boat scenes, which took place on the Miles River, required careful coordination and planning to ensure the safety of the cast and crew. The team had to navigate the complexities of filming on a moving boat while capturing the chemistry between the actors. The end result was a visually stunning sequence that added depth and romance to the film.</p>
<p class="editor-paragraph" dir="ltr">"Clara's Heart" presented its own set of challenges, particularly in capturing the essence of the Eastern Shore's rural landscapes. The filmmakers had to work closely with the local community to find the perfect locations and ensure an authentic representation of the region. The collaboration between the filmmakers and the locals added an extra layer of authenticity to the film, elevating the storytelling and creating a powerful emotional connection with the audience.</p>
</div>
</div>
<div>
<h3>Film Festivals and Events Celebrating the Eastern Shore's Cinematic History</h3>
<div>
<p class="editor-paragraph" dir="ltr">The Eastern Shore's rich cinematic history is celebrated through various film festivals and events that showcase the region's connection to the movie industry. These festivals provide a platform for filmmakers, actors, and film enthusiasts to come together and celebrate the art of cinema.</p>
<p class="editor-paragraph" dir="ltr">One of the most notable film festivals on the Eastern Shore is the Chesapeake Film Festival. This annual event showcases independent films from around the world, with a focus on stories that capture the essence of the Chesapeake Bay region. The festival attracts filmmakers, actors, and film enthusiasts from all over the country, creating a vibrant creative community on the Eastern Shore.</p>
<p class="editor-paragraph" dir="ltr">In addition to the Chesapeake Film Festival, there are also smaller events and screenings that celebrate the Eastern Shore's cinematic history. Local theaters and community organizations often host film screenings and discussions, providing an opportunity for the community to come together and appreciate the films shot in their own backyard.</p>
<p class="editor-paragraph" dir="ltr">These film festivals and events not only celebrate the films shot on the Eastern Shore but also inspire and nurture local talent. They provide a platform for emerging filmmakers to showcase their work and connect with industry professionals, fostering a vibrant creative community on the Eastern Shore.</p>
</div>
</div>
<div>
<h3>Conclusion: The Enduring Appeal of Maryland's Eastern Shore as a Movie-Making Destination</h3>
<div>
<p class="editor-paragraph" dir="ltr">Maryland's Eastern Shore has captivated filmmakers for decades with its rustic appeal, stunning landscapes, and authentic atmosphere. From iconic comedies like "Wedding Crashers" to heartfelt dramas like "Clara's Heart," the region has provided the perfect backdrop for a wide range of films.</p>
<p class="editor-paragraph" dir="ltr">The success of these films has not only put Maryland's Eastern Shore on the map as a desirable filming location but also boosted the local economy and tourism industry. Visitors from all over the country have flocked to the Eastern Shore to experience the charm and beauty showcased in these films, supporting local businesses and creating job opportunities for the community.</p>
<p class="editor-paragraph" dir="ltr">The Eastern Shore's cinematic history is celebrated through film festivals and events that highlight the region's connection to the movie industry. These events not only showcase the films shot in the area but also inspire and nurture local talent, creating a vibrant creative community.</p>
<p class="editor-paragraph" dir="ltr">As we explore the legendary films shot on Maryland's Eastern Shore, we are reminded of the enduring appeal of this captivating coastal haven. Its unique blend of natural beauty, historic architecture, and authentic atmosphere continues to attract filmmakers, ensuring that the magic of the movies will continue to be captured on the shores of Maryland for years to come.</p>
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Films Shot on Maryland's Eastern Shore - Oxford, St. Michaels, and Easton

Welcome to a captivating journey into the heart of Maryland's Eastern Shore! Our latest blog post, "Exploring Movie Magic: Legendary Films Shot on Maryland's Eastern Shore," invites you to step behind the camera and uncover the scenic beauty that has made this picturesque region a magnet for filmmakers.

From the charming coastal towns of Oxford, St. Michaels, and Easton to the sweeping landscapes that seem to whisper stories of times gone by, the Eastern Shore of Maryland has been the backdrop for some of Hollywood's most memorable cinematic moments. Whether you're a die-hard film buff or just someone who appreciates the spellbinding charm of the Eastern Shore, this post offers a fascinating glimpse into the movies that have captured the essence of this unique locale.

Join us as we delve into the history, charm, and natural beauty that have drawn directors and producers to this quaint yet captivating part of the world. With each paragraph, you'll discover the behind-the-scenes anecdotes, the famous films shot in the region, and the impact these productions have had on the local community and its economy.

So grab some popcorn, settle in, and let us guide you on an enchanting tour of Maryland's Eastern Shore through the lens of the cinematic world. It's time to discover the movie magic that continues to make this coastal haven an unforgettable destination for filmmakers and visitors alike.

Explore the movies filmed on Maryland’s Eastern Shore, from Oxford and St. Michaels to Easton. Discover the scenic waterfronts, historic towns, and cinematic landscapes that have attracted filmmakers for decades — including iconic Hollywood productions.

Movies Filmed on Maryland’s Eastern Shore: Oxford, St. Michaels & Easton

<h1 data-path-to-node="3">Launch the Next Chapter of Your Love Story at Sandaway Suites &amp; Beach</h1>
<p data-path-to-node="4">Oxford, Maryland, is famous for its timeless coastal elegance and breathtaking sunsets&mdash;the very qualities that drew Hollywood right to our shores! Our quaint town served as a key filming location for the romantic comedy <strong><em>Failure to Launch</em></strong>, starring Matthew McConaughey and Sarah Jessica Parker. Just as the movie characters sought a change of scenery to find their next chapter, Sandaway Suites &amp; Beach offers the perfect, secluded stage for <strong>you</strong> to launch yours.</p>
<h2 data-path-to-node="5">Behind the Scenes: The Day Hollywood Came to Oxford</h2>
<p data-path-to-node="6">The film crew didn't just casually pass through Oxford&mdash;they <em>lived</em> here! To create the perfect scenes for <em>Failure to Launch</em>, the production team essentially transformed key parts of the town for several weeks of shooting.</p>
<p data-path-to-node="7">While the bulk of the film was shot in New Orleans, the most visually charming and pivotal scenes required Oxford&rsquo;s unique seaside atmosphere. Filming was tightly scheduled for locations like <strong>Bachelor's Point</strong>, <strong>The Masthead at Pier Street</strong>, and the local <strong>Oxford Boatyard</strong>, with work also taking place at <strong>Cutts &amp; Case Inc.</strong></p>
<h2 data-path-to-node="8"><strong>The Famous Yacht Scene:</strong></h2>
<p data-path-to-node="9">One of the most memorable scenes shot right here at the Oxford Boatyard features Matthew McConaughey's character, Trippe, trying to impress Sarah Jessica Parker's character, Paula, by taking her out on a luxury yacht. In classic romantic comedy style, the moment is ruined when the actual boat owner shows up and unceremoniously kicks them off&mdash;a hilarious snapshot of the film&rsquo;s central conflict!</p>
<p data-path-to-node="10"><strong>A Major Production:</strong></p>
<p data-path-to-node="11">This was no small affair! The film, directed by Tom Dey (<em>Shanghai Noon</em>) and produced by Scott Rudin (<em>The Truman Show</em>), brought a cast and crew of about <strong>170 people</strong> to Oxford. Many worked on the hit movie <em>Wedding Crashers</em> the previous year, highlighting that Hollywood consistently chooses Talbot County for its perfect romantic backdrops. It took extensive preparation, including "peel painting" boats to temporarily change their look for the cameras.</p>
<h2 data-path-to-node="12">Live Like the Film Crew</h2>
<p data-path-to-node="13">During the weeks of filming, the large cast and crew needed quiet, comfortable accommodations close to the water. Our very own <strong>Sandaway Suites &amp; Beach had the distinct pleasure of hosting some of the film crew</strong> right here on our secluded, romantic property.</p>
<p data-path-to-node="14">When you choose Sandaway, you are literally choosing the same idyllic, waterfront charm that Hollywood producers selected for a major romantic film. Imagine the inspiration that sparked on the very lawn where you could say "I do" or pop the ultimate question!</p>
<h2 data-path-to-node="15">Your Romantic Oxford "Failure to Launch" Location Tour</h2>
<p data-path-to-node="16">While you&rsquo;re here launching your own love story, why not enjoy a little local sightseeing? You can plan a charming, romantic walking tour right from Sandaway to visit some of the key spots in Oxford featured in the movie. It&rsquo;s the perfect way to spend an afternoon capturing fun, film-inspired photos together!</p>
<p data-path-to-node="16">Shooting locations in Oxford, Maryland included in the <em><strong>Failure to Launch</strong></em> movie production intineray were Bachelor&rsquo;s Point, Oxford Boatyard, Masthead at Pier Street (Now Doc's Sunset Grille), and Cutts &amp; Case Shipyard.</p>
<ol start="1" data-path-to-node="17">
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<p data-path-to-node="17,0,0"><strong>The Iconic Dock Scenes (Now Doc's Sunset Grille):</strong></p>
<ul data-path-to-node="17,0,1">
<li>
<p data-path-to-node="17,0,1,0,0"><strong>What you saw:</strong> Many of the most memorable boat and dock scenes, including where they filmed the dockside restaurant what is now "Doc's Sunset Grille" and Oxford Boatyard.</p>
</li>
<li>
<p data-path-to-node="17,0,1,1,0"><strong>Your tour moment:</strong> Take a sunset stroll down these historic piers. Imagine the cinematic moments that unfolded against the Chesapeake Bay backdrop and recreate your own romantic scene looking out over the water.</p>
</li>
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</li>
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<p data-path-to-node="17,1,0"><strong>The Town Charm (Historic Oxford, Maryland):</strong></p>
<ul data-path-to-node="17,1,1">
<li>
<p data-path-to-node="17,1,1,0,0"><strong>What you saw:</strong> The picturesque, historic streets and charming homes in the main part of Oxford served as the backdrop for numerous scenes.</p>
</li>
<li>
<p data-path-to-node="17,1,1,1,0"><strong>Your tour moment:</strong> Walk hand-in-hand down <strong>Morris Street</strong>. Admire the beautiful architecture and imagine yourselves as the stars of your own romantic comedy while enjoying the town's tranquil atmosphere.</p>
</li>
</ul>
</li>
<li>
<p data-path-to-node="17,2,0"><strong>The Sailing Views (The Montages):</strong></p>
<ul data-path-to-node="17,2,1">
<li>
<p data-path-to-node="17,2,1,0,0"><strong>What you saw:</strong> The beautiful shots of sailboats gliding on the open water, which emphasize the breezy, romantic lifestyle, were captured right here on the <strong>Tred Avon River</strong> and the <strong>Choptank River</strong>.</p>
</li>
<li>
<p data-path-to-node="17,2,1,1,0"><strong>Your tour moment:</strong> These views are best enjoyed right from the comfort of <strong>Sandaway's private beach and waterfront lawn!</strong> Relax in an Adirondack chair with a drink and watch the sailboats go by, taking in the same panoramic, cinematic water views the filmmakers sought out.</p>
</li>
</ul>
</li>
</ol>
<h2 data-path-to-node="18">Your Success Story Starts Here</h2>
<p data-path-to-node="19">Don't suffer from a "failure to launch" your romantic plans! Sandaway Suites &amp; Beach offers the seclusion, beauty, and intimacy needed to make your proposal or intimate wedding absolutely unforgettable. We are the perfect <strong>Hollywood-approved launchpad</strong> for your next great adventure.</p>
<ul data-path-to-node="20">
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<p data-path-to-node="20,0,0"><strong>A Private Beach for "I Do"s:</strong> Our exclusive, secluded beach is ideal for a heartfelt proposal or a stunning, intimate waterfront ceremony.</p>
</li>
<li>
<p data-path-to-node="20,1,0"><strong>Romantic Suites:</strong> Our adult-only suites are designed for pure relaxation and reconnection, offering water views and a peaceful escape.</p>
</li>
</ul>
<p data-path-to-node="21">We offer specialized Romance and Proposal Packages to help you craft the perfect moment without any stress. Let us take care of the details while you prepare to launch into the most exciting chapter of your love story!</p>
<p data-path-to-node="21">Visit Sandaway Suites &amp; Beach official wedding page for Sunset Ceremony or Proposal Packages&nbsp;<a href="https://www.sandaway.com/weddings/">https://www.sandaway.com/weddings/</a></p>
<p data-path-to-node="21">&nbsp;</p>

<h3 data-path-to-node="2">Trailer Summary: <em>Failure to Launch</em> (2006)</h3>
<p data-path-to-node="3">The trailer for <em>Failure to Launch</em> quickly sets up the central, humorous conflict:</p>
<ul data-path-to-node="4">
<li>
<p data-path-to-node="4,0,0"><strong>The Problem:</strong> Trippe (Matthew McConaughey) is 35 years old and still lives at home with his parents, who are desperate for him to move out [<a class="ng-star-inserted" href="http://www.youtube.com/watch?v=evzBwXvqEl4&amp;t=25" target="_blank" rel="noopener" data-hveid="0" data-ved="0CAAQ_4QMahgKEwiqwpnFtb6RAxUAAAAAHQAAAAAQ4QE">00:25</a>].</p>
</li>
<li>
<p data-path-to-node="4,1,0"><strong>The Solution:</strong> They hire Paula (Sarah Jessica Parker), a professional "motivator," to start a romantic relationship with Trippe, boosting his self-esteem until he is ready to leave the nest [<a class="ng-star-inserted" href="http://www.youtube.com/watch?v=evzBwXvqEl4&amp;t=36" target="_blank" rel="noopener" data-hveid="0" data-ved="0CAAQ_4QMahgKEwiqwpnFtb6RAxUAAAAAHQAAAAAQ4gE">00:36</a>].</p>
</li>
<li>
<p data-path-to-node="4,2,0"><strong>The Complications:</strong> Paula is an expert at creating a relationship that will eventually push him away (she details her strategy for a first date, including ordering a huge dessert and talking about old boyfriends [<a class="ng-star-inserted" href="http://www.youtube.com/watch?v=evzBwXvqEl4&amp;t=55" target="_blank" rel="noopener" data-hveid="0" data-ved="0CAAQ_4QMahgKEwiqwpnFtb6RAxUAAAAAHQAAAAAQ4wE">00:55</a>]). However, she soon realizes she genuinely likes Trippe, and the line between the professional arrangement and real feelings starts to blur [<a class="ng-star-inserted" href="http://www.youtube.com/watch?v=evzBwXvqEl4&amp;t=109" target="_blank" rel="noopener" data-hveid="0" data-ved="0CAAQ_4QMahgKEwiqwpnFtb6RAxUAAAAAHQAAAAAQ5AE">01:49</a>].</p>
</li>
<li>
<p data-path-to-node="4,3,0"><strong>The Stakes:</strong> The parents and Paula's team start to panic as the relationship deviates from the plan, leading to a race against time and a final realization that Trippe must conquer his fear of love and <em>launch</em> after Paula [<a class="ng-star-inserted" href="http://www.youtube.com/watch?v=evzBwXvqEl4&amp;t=125" target="_blank" rel="noopener" data-hveid="0" data-ved="0CAAQ_4QMahgKEwiqwpnFtb6RAxUAAAAAHQAAAAAQ5QE">02:05</a>].</p>
</li>
</ul>

Launch the Next Chapter of Your Love Story

Oxford, Maryland, is famous for its timeless coastal elegance and breathtaking sunsets—the very qualities that drew Hollywood right to our shores! Our quaint town served as a key filming location for the romantic comedy Failure to Launch, starring Matthew McConaughey and Sarah Jessica Parker. Just as the movie characters sought a change of scenery to find their next chapter, Sandaway Suites & Beach offers the perfect, secluded stage for you to launch yours. Discover how our beautiful, waterfront property—where some of the film crew even stayed—provides the ideal, cinematic backdrop for your unforgettable proposal, intimate wedding, or deeply romantic getaway.

Discover why Hollywood chose Oxford, MD (Failure to Launch filming location) for romance. Start your next chapter with a proposal or intimate wedding at Sandaway Suites & Beach.