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Eastern Shore Getaways | Top Virginia Adventures For Outdoor Travelers


Modified: December 27, 2023

by Janot Carver



Welcome to the Eastern Shore, a hidden gem for outdoor enthusiasts and adventure seekers in Virginia. Nestled between the Chesapeake Bay and the Atlantic Ocean, this region offers a diverse range of activities and attractions for those craving an unforgettable outdoor experience. From pristine beaches and wildlife refuges to charming coastal towns and scenic trails, the Eastern Shore has something for everyone.


Whether you’re a nature lover, a water sports enthusiast, or simply seeking a tranquil escape, the Eastern Shore will mesmerize you with its natural beauty and abundant recreational opportunities. With its stunning shoreline, unique wildlife, and rich history, this region promises an exciting and immersive adventure that will leave you in awe.


So, lace up your hiking boots, grab your kayak, and get ready to explore the top Virginia adventures on the Eastern Shore. In this article, we’ll take you on a journey through the must-visit destinations and activities that will make your outdoor travel experience truly unforgettable.


Virginia Beach

When it comes to beach destinations on the Eastern Shore, Virginia Beach undoubtedly tops the list. With its pristine sandy shores stretching for miles, it offers the perfect setting for sunbathing, swimming, and an array of water sports. Whether you’re a beginner or an experienced surfer, the waves here are ideal for catching a thrilling ride.


For those seeking a more laid-back experience, take a leisurely stroll along the famous Virginia Beach Boardwalk. Lined with shops, restaurants, and entertainment venues, it’s the perfect place to soak up the lively atmosphere and enjoy stunning ocean views.


But Virginia Beach isn’t just about beach activities. The nearby First Landing State Park is a nature lover’s paradise. Explore over 19 miles of hiking trails that wind through lush forests, dunes, and marshes. Keep an eye out for wildlife, including deer, foxes, and a wide variety of bird species.


Thrill-seekers can also take advantage of the many water sports opportunities. From kayaking and paddleboarding to jet skiing and parasailing, there’s something for everyone. And if you’re feeling adventurous, why not try your hand at deep-sea fishing and reel in your own catch of the day?


When hunger strikes, you’ll find no shortage of restaurants offering fresh seafood specialties. From seafood shacks serving up mouthwatering crab cakes to elegant waterfront establishments, your taste buds are in for a treat.


As the day winds down, don’t miss the chance to witness a breathtaking sunset over the Atlantic Ocean. Find a cozy spot on the beach, sit back, and let the vibrant colors paint the sky. It’s a picture-perfect ending to a day in Virginia Beach.


Assateague Island

Located just off the coast of Virginia and Maryland, Assateague Island is a must-visit destination for nature lovers and wildlife enthusiasts. This barrier island is known for its untouched natural beauty, wild horses, and pristine beaches. As you step foot on Assateague, you’ll feel like you’ve entered a different world, far removed from the hustle and bustle of everyday life.


The highlight of Assateague Island is undoubtedly the wild horses. These majestic creatures roam freely across the island, grazing in the marshes and dunes. You can catch a glimpse of these beautiful animals as you hike along the trails or relax on the beach. Remember to maintain a safe distance and observe them from afar, as they are wild and should not be approached.


Speaking of beaches, Assateague Island boasts miles of untouched shoreline. With its rolling sand dunes and crystal-clear waters, it’s a paradise for beach lovers. Whether you prefer swimming, sunbathing, or beachcombing for seashells, Assateague offers a tranquil and secluded escape.


If you’re up for an adventure, rent a kayak or canoe and explore the calm waters of the island’s bays and estuaries. Paddle through narrow channels, spot different bird species, and immerse yourself in the peaceful serenity of the island’s natural habitats.


For a deeper understanding of the island’s unique ecosystem, visit the Assateague Island Visitor Center. Here, you’ll find interactive exhibits, educational programs, and ranger-led activities that delve into the island’s history, wildlife, and conservation efforts.


Camping is popular on Assateague Island, with both tent and RV camping options available. Fall asleep under a starlit sky and let the sounds of nature serenade you to sleep. It’s an experience like no other.


Finally, don’t miss the chance to witness a spectacular sunrise or sunset on Assateague Island. The island’s untouched landscapes provide the perfect backdrop for breathtaking moments that will stay with you long after you leave.


Chincoteague National Wildlife Refuge

Located on the southern end of Assateague Island, Chincoteague National Wildlife Refuge is a haven for birdwatchers, nature enthusiasts, and outdoor explorers. Spread across 14,000 acres of pristine coastal habitat, this refuge offers a unique opportunity to observe an incredible variety of wildlife in their natural environment.


The refuge is home to over 300 bird species, making it a birdwatcher’s paradise. From elegant egrets and great blue herons to colorful migratory birds, there’s always something to see. Grab your binoculars and head to one of the many observation platforms or take a leisurely stroll along the wildlife trails for an up-close encounter with these magnificent creatures.


One of the most popular attractions at Chincoteague National Wildlife Refuge is the annual Pony Swim. Each July, the wild horses of Assateague Island are rounded up and swim across the channel to Chincoteague Island, where they are auctioned off to ensure the herd’s population remains sustainable. This unique event draws visitors from all over the country to witness this unforgettable sight.


Outside of the Pony Swim, Chincoteague Island is known for its quaint charm and unique local culture. Explore the vibrant downtown area with its boutique shops, art galleries, and seafood restaurants. Don’t forget to indulge in the region’s famous Chincoteague oysters, a delicacy that epitomizes the flavors of the Eastern Shore.


If you’re seeking outdoor adventures, Chincoteague National Wildlife Refuge offers several recreational activities. Bike along the paved Wildlife Loop, embarking on a scenic journey that offers glimpses of the marshes, woods, and tidal ponds. Paddle through the refuge’s waterways, keeping an eye out for playful dolphins and other marine creatures.


For a truly immersive experience, consider camping at the refuge’s campgrounds. Fall asleep to the sound of waves crashing on the shore, wake up to the melodies of birds, and feel the serenity of nature surrounding you.


Chincoteague National Wildlife Refuge is a sanctuary for both wildlife and those seeking a peaceful retreat away from the pressures of urban life. So, pack your camera, grab your binoculars, and get ready for an adventure that will leave you in awe of the natural wonders of the Eastern Shore.


The Chesapeake Bay Bridge-Tunnel

Prepare to embark on a truly remarkable engineering feat – the Chesapeake Bay Bridge-Tunnel. Spanning over 20 miles, this incredible structure connects the shorelines of Virginia’s Eastern Shore and the mainland, allowing travelers to cross the vast expanse of the Chesapeake Bay.


Driving across the bridge-tunnel is an awe-inspiring experience. As you traverse the meticulously constructed segments, you’ll be treated to breathtaking views of the open waters, vast sky, and magnificent sunsets. Keep your eyes peeled for passing ships, dolphins playing in the bay, and even the occasional whale sighting.


Make sure to make use of the designated parking areas along the bridge-tunnel for some truly spectacular photo opportunities. Capture memories against the backdrop of this engineering marvel that seamlessly integrates with nature’s beauty.


For a more immersive experience, take advantage of guided tours that provide insights into the history, construction, and operation of the Chesapeake Bay Bridge-Tunnel. Learn about the challenges faced during its construction and marvel at the inventive solutions employed to create this icon of Virginia.


Anglers will find numerous fishing platforms along the bridge-tunnel where they can cast their lines and try their luck at catching various species of fish. Whether you’re a novice or an experienced angler, the bridge-tunnel offers a unique angling experience amidst the stunning backdrop of the Chesapeake Bay.


As you approach the end of the Chesapeake Bay Bridge-Tunnel, you’ll find yourself at the gateway to Virginia’s Eastern Shore. Take the time to explore the charming towns and picturesque landscapes that await you on this side of the bay. From historic sites and quaint shops to delicious local cuisine, the Eastern Shore has plenty to offer.


Whether you’re just passing through or taking a leisurely drive, the Chesapeake Bay Bridge-Tunnel is an iconic landmark that showcases the natural beauty of the region and offers an unforgettable experience for all who traverse its majestic path.


Cape Charles

Tucked away on the southern tip of Virginia’s Eastern Shore, Cape Charles is a charming coastal town that offers a perfect blend of history, natural beauty, and laid-back charm. With its pristine beaches, quaint streets lined with Victorian-era homes, and a vibrant downtown, Cape Charles is a hidden gem just waiting to be discovered.


One of the main draws of Cape Charles is its picturesque beach, which stretches for miles along the Chesapeake Bay. Here, you can soak up the sun, take a refreshing swim, or simply stroll along the soft sands while enjoying views of the bay and the distant bridge-tunnel.


For those seeking outdoor adventures, Cape Charles has plenty to offer. Rent a bike and explore the town and its surroundings, or try your hand at fishing off the town’s fishing pier. If you’re a golf enthusiast, you’ll find a well-regarded golf course that overlooks the Chesapeake Bay.


History buffs will appreciate a visit to the Cape Charles Museum and Welcome Center, which showcases the town’s rich heritage and maritime history. Learn about the town’s role as a railroad and steamship hub, and explore exhibits that highlight the area’s unique culture and heritage.


As you wander through downtown Cape Charles, you’ll be captivated by its small-town charm. Browse the boutique shops, art galleries, and antique stores that line the streets. Grab a bite to eat at one of the waterfront restaurants serving up fresh seafood and local specialties.


For a unique experience, consider taking a sunset cruise or a fishing charter from the Cape Charles Harbor. Feel the gentle breeze as you sail along the Chesapeake Bay, marveling at the vibrant colors of the setting sun against the backdrop of the water.


In the evenings, don’t miss the opportunity to catch live music or performances at the town’s charming venues. From local bands to nationally acclaimed artists, Cape Charles offers a vibrant arts and entertainment scene that will leave you wanting more.


Cape Charles truly captures the essence of coastal living. Whether you’re seeking relaxation on the beach, exploring the rich history of the area, or immersing yourself in the local culture, this charming town is sure to leave you with lasting memories and a desire to return time and time again.


Tangier Island

Nestled in the Chesapeake Bay, Tangier Island is a true hidden gem that offers visitors a glimpse into a unique way of life. With its remote location and rich history, this small island has become a popular destination for those seeking a peaceful retreat and a taste of authentic Eastern Shore culture.


One of the most captivating aspects of Tangier Island is its distinct community and accent. The islanders, known as “Tangiermen,” are descendants of a small group of settlers who arrived in the 17th century. Their isolation from the mainland has preserved their unique way of life and traditional Chesapeake Bay dialect, making a visit to Tangier feel like stepping back in time.


Explore the island by foot, bicycle, or rent a golf cart to navigate the narrow streets. As you wander through the quaint town, you’ll be greeted by locals who embody the legendary Chesapeake Bay hospitality. Strike up a conversation and learn about their way of life, which revolves around crabbing, fishing, and harvesting oysters.


For a deeper understanding of the island’s rich history and culture, visit the Tangier History Museum and Interpretive Cultural Center. Discover the island’s maritime heritage, learn about the island’s connection to the War of 1812, and gain insights into the environmental challenges facing Tangier today.


Don’t miss the chance to savor the bounty of the Chesapeake Bay with a seafood feast. Tangier Island is renowned for its delicious seafood, especially the mouthwatering Chesapeake Bay blue crabs and the locally harvested oysters. Indulge in a crab cake sandwich or enjoy a plate of freshly steamed crabs, all while taking in the mesmerizing views of the bay.


For nature lovers, Tangier Island offers an abundance of natural beauty to explore. Take a leisurely bike ride or hike along the island’s trails and be rewarded with stunning vistas of marshes, open fields, and pristine beaches. Keep an eye out for the incredible array of bird species that inhabit the island and its surrounding waters.


To truly immerse yourself in the island’s charm, consider staying overnight at one of the cozy bed and breakfasts or rental cottages. Wake up to the gentle sounds of the bay, enjoy a homemade breakfast, and soak in the serene atmosphere that Tangier Island exudes.


A visit to Tangier Island is a step into a different world, where time seems to slow down and the connection to nature and community is paramount. Experience the magic of this remote island and create memories that will last a lifetime.


Kiptopeke State Park

Situated on the southern end of Virginia’s Eastern Shore, Kiptopeke State Park offers nature lovers and outdoor enthusiasts a stunning coastal retreat filled with breathtaking views and a variety of recreational activities.


One of the park’s main draws is its pristine sandy beach, which stretches along the Chesapeake Bay for over a mile. Whether you’re looking to swim in the refreshing waters, build sandcastles with your family, or simply relax and soak up the sun, Kiptopeke State Park provides the perfect beach escape.


The park is also renowned for its excellent fishing opportunities. Cast your line from the fishing pier and try your luck at catching a variety of fish, including flounder, croaker, and spot. If you prefer to fish from your boat, the park has boat ramps available for launching your vessel into the bay.


For those who enjoy birdwatching, Kiptopeke State Park is a haven. The park is situated along the Atlantic Flyway, making it a prime location for observing migratory birds. Keep your binoculars handy, as you may spot a variety of species, including warblers, raptors, and waterfowl.


If you’re seeking a more active adventure, the park offers hiking and biking trails that wind through the coastal forest and marshes. Immerse yourself in the natural beauty surrounding you as you explore these serene pathways, keeping an eye out for native wildlife along the way.


Kiptopeke State Park also offers a range of camping options, including tent and RV sites, as well as cozy cabins nestled within the park’s tranquil setting. Fall asleep to the soothing sound of waves crashing on the shoreline and wake up to the songs of birds greeting the day.


During your visit, be sure to check out the park’s visitor center, where you can learn more about the natural and cultural history of the area. Exhibits and displays provide valuable insights into the diverse ecosystems and wildlife that call Kiptopeke home.


As the day comes to a close, find a comfortable spot to witness a breathtaking sunset over the Chesapeake Bay. Watch as the sky transforms into a canvas of vibrant oranges, pinks, and purples, casting a magical glow over the water.


Experience the natural wonders of Virginia’s Eastern Shore at Kiptopeke State Park, where outdoor adventures and tranquil surroundings await. Whether you’re seeking relaxation, recreational activities, or wildlife encounters, this coastal gem has it all.


First Landing State Park

Nestled at the mouth of the Chesapeake Bay, First Landing State Park is a coastal paradise that offers visitors a diverse range of outdoor activities and a glimpse into the area’s rich history. As Virginia’s most visited state park, First Landing is a haven for nature lovers, history buffs, and outdoor enthusiasts.


The park’s pristine beaches are a major attraction. With over 1.5 miles of sandy shoreline, you can enjoy swimming, sunbathing, or simply strolling along the water’s edge. The calm waters of Chesapeake Bay make it ideal for paddleboarding, kayaking, and even crabbing.


In addition to its beach, First Landing State Park boasts over 19 miles of hiking trails that wind through a variety of landscapes, including marshes, dunes, and forests. Trek along the Cape Henry Trail, which takes you through diverse ecosystems and provides spectacular views of the bay. Keep your eyes peeled for wildlife sightings, including deer, foxes, and a variety of bird species.


History enthusiasts will appreciate the park’s connection to early American history. First Landing State Park is believed to be the site of the first landing of English colonists in 1607, prior to their journey to Jamestown. Explore the park’s interpretive programs and exhibits to learn about the region’s indigenous people and the earliest European settlers.


If you’re interested in camping, the park offers options for both tent and RV camping. Wake up to the sounds of birdsong and the scent of the coastal breeze, surrounded by the beauty of nature.


For a unique experience, consider taking a guided kayak or canoe tour through the park’s waterways. Paddle through cypress swamps and tidal marshes, immersing yourself in the tranquility and natural beauty of the area.


First Landing State Park also offers picnic areas, a visitor center, and a gift shop where you can find unique souvenirs and educational materials about the park’s natural and cultural resources.


Whether you’re seeking adventure, relaxation, or an educational experience, First Landing State Park has it all. Immerse yourself in the natural beauty and fascinating history of this coastal gem, and create memories that will last a lifetime.


Eastern Shore National Wildlife Refuge

The Eastern Shore National Wildlife Refuge, located on Virginia’s Eastern Shore, is a haven for wildlife enthusiasts and nature lovers. This expansive refuge spans over 1,100 acres and provides a vital sanctuary for migratory birds, endangered species, and a diverse array of plant and animal life.


One of the key highlights of the Eastern Shore National Wildlife Refuge is its exceptional birdwatching opportunities. As part of the Atlantic Flyway, the refuge attracts an impressive number of migrating birds. From majestic bald eagles and ospreys to colorful warblers and waterfowl, birdwatchers will be treated to an amazing spectacle of avian activity.


Explore the refuge on over six miles of walking trails that wind through various habitats, including marshes, woodlands, and fields. Along these scenic trails, you may encounter wildlife such as deer, foxes, turtles, and a variety of bird species. Don’t forget your binoculars and camera to capture the beauty of these natural wonders.


The refuge also offers a select number of hunting opportunities during waterfowl and deer seasons. Hunters must adhere to strict regulations and obtain the necessary permits to participate in these activities, ensuring the conservation of the refuge’s wildlife populations.


If you’re interested in learning more about the region’s flora and fauna, visit the refuge’s visitor center. Here, you’ll find informative exhibits on the diverse habitats found within the refuge, as well as educational programs and guided nature walks led by knowledgeable staff and volunteers.


For a unique perspective of the refuge, consider exploring it by water. Rent a kayak or canoe and paddle through the tranquil waterways, immersing yourself in the serenity of the marshes and observing wildlife up close in their natural habitat.


With its commitment to conservation, the Eastern Shore National Wildlife Refuge plays a crucial role in protecting and preserving the region’s natural heritage. It offers visitors the opportunity to reconnect with nature, appreciate the ecological importance of wetlands, and witness the beauty of wildlife thriving in their natural environment.


If you’re seeking a serene and immersive experience in nature, a visit to the Eastern Shore National Wildlife Refuge is a must. Explore the trails, marvel at the diversity of birdlife, and discover the wonders of this remarkable refuge.


Eastern Shore Rail Trail

The Eastern Shore Rail Trail is a hidden gem for outdoor enthusiasts and cycling enthusiasts on Virginia’s Eastern Shore. This scenic trail spans approximately 23 miles and follows the path of a former railroad line, offering a unique and picturesque journey through the region’s breathtaking landscapes.


Whether you’re an avid cyclist or a casual rider, the Eastern Shore Rail Trail provides a safe and enjoyable route. The mostly flat terrain and well-maintained surface make it accessible to riders of all skill levels. Grab your bike and embark on an adventure that showcases the natural beauty and cultural heritage of the Eastern Shore.


As you pedal along the trail, you’ll be captivated by the stunning panoramic views of farmland, wetlands, and wooded areas. The peaceful atmosphere and tranquility of the surroundings create the perfect setting for a leisurely ride or an invigorating workout.


Along the Eastern Shore Rail Trail, you’ll find rest areas with benches and interpretive signs that offer insights into the region’s history and ecology. Learn about the fascinating railroad history and the impact it had on the development of the Eastern Shore. Keep an eye out for wildlife sightings, as the trail is known to attract a variety of birds, butterflies, and other animals.


The trail passes through charming towns and communities, providing opportunities to stop and explore. Discover local shops, restaurants, and attractions that showcase the Eastern Shore’s unique culture and hospitality. Take a break and sample delicious regional cuisine or browse the artwork and handicrafts crafted by local artisans.


For those who prefer hiking or walking, the Eastern Shore Rail Trail accommodates pedestrians as well. Lace up your walking shoes and enjoy a scenic stroll, taking in the beauty of the surrounding nature at a relaxed pace.


Bring your camera along as you may encounter breathtaking photo opportunities along the trail. Capture the vibrant colors of wildflowers, the serenity of wetlands, and the quaint architecture of Eastern Shore communities.


Whether you’re seeking a solo adventure or a memorable family outing, the Eastern Shore Rail Trail offers a truly immersive and enjoyable experience. So, hop on your bike, breathe in the fresh air, and let the Eastern Shore’s natural wonders and cultural treasures unfold before your eyes.



The Eastern Shore of Virginia is a treasure trove of outdoor adventures and natural wonders waiting to be explored. From the sandy beaches of Virginia Beach to the untamed beauty of Assateague Island, and from the charming coastal towns like Cape Charles to the serene landscapes of First Landing State Park, the Eastern Shore offers a diverse range of experiences for outdoor enthusiasts and adventure seekers.


Whether you choose to indulge in water sports, hike along scenic trails, observe wildlife in their natural habitats, or simply relax on the beach and soak in the coastal atmosphere, the Eastern Shore has something to offer everyone. The region’s rich history, vibrant culture, and abundant wildlife create an immersive and memorable experience for visitors of all ages.


From the captivating wild horses of Assateague Island to the engineering marvel of the Chesapeake Bay Bridge-Tunnel and the tranquility of Kiptopeke State Park, each destination on the Eastern Shore offers its own unique charm and adventure.


Immerse yourself in the natural beauty of the Eastern Shore National Wildlife Refuge, explore the cultural heritage of Cape Charles, and pedal along the scenic Eastern Shore Rail Trail. Witness spectacular sunsets, sample fresh seafood, and engage with the warm and welcoming local communities.


Whether you’re seeking relaxation, outdoor thrills, or a deeper connection with nature, the Eastern Shore of Virginia promises an unforgettable adventure. So, pack your bags, lace up your hiking boots, and embark on a journey to this captivating and awe-inspiring region. Discover the hidden gems, create lifelong memories, and fall in love with the beauty of the Eastern Shore.