First Landing: Kayaking Virginia's Historical Coast

Sierra Club Outings Trip # 14075A, Kayak


  • Kayak the unique and diverse waterways of coastal Virginia
  • Enjoy miles of Chesapeake Bay beach and nature trails
  • Explore Great Dismal Swamp NWR and Back Bay NWR


  • Kayak, paddle, and PFD/life jacket rental
  • Six nights lodging in cozy cabins near beach and trails
  • Most meals


DatesMay 11–17, 2014
StaffJohn Kovacevic

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Trip Overview

The Trip

Coastal Virginia is a landscape of intimate natural diversity.

The coastal plain flows east from the fall line and forms a maze of hundreds of rivers, creeks, freshwater and saltwater marshes, cypress swamps, salty bays, and barrier islands.

Names like Blackwater River, West Neck Creek, or Great Dismal Swamp will not ring a bell for most people. After kayaking these and other diverse waterways, you will leave each with reluctance, not knowing if you will find another one quite as beautiful. The beauty of these waterways manifests itself in numerous ways: searching for ospreys and other wildlife while paddling a clear blue bay; having a dolphin surface nearby as you gently dip your paddle in and out of the water; being stunned by the majestic strangeness, primitiveness and quiet of an ancient cypress swamp; paddling though the delicate beauty of a winding waterway engulfed in marsh; paddling past centuries old trees that line the shoreline, wishing that they could speak to us and tell us countless stories of times past. Coastal Virginia contains a blend of waterways, trails, beach, and history that offers a real opportunity for modern day exploration.

In 1607, after many long days at sea, a landing party from several English ships came ashore and climbed the high sand dunes at Cape Henry. They decided to travel farther inland to find a more protected site, which led to the founding of Jamestown. After several failed attempts, including the lost colony of Roanoke, Jamestown became the first permanent English colony in the New World. The colonists later returned to Cape Henry and erected a wooden cross to mark their “first landing.” First Landing State Park, Virginia is located in the same area that the English colonists first arrived at. Although the landscape of the surrounding area has drastically changed from 1607 to the present, there is still much that remains in a natural state that beckons us to explore it. The modern day explorer will be just as amazed at the diversity and beauty of the historical coastal Virginia landscape as were the early colonists. First Landing State Park has earned a spot on the National Register of Natural Landmarks because it contains the northernmost mix of subtropical and temperate habitats on the East Coast. These natural areas include cypress swamps, maritime forests, pine/beech forests, sand dunes, salt marsh, beach, and bay. First Landing State Park will be our base camp for our kayaking adventure on Virginia’s historical coast. After a day of kayaking and exploring, we return daily to a setting that offers over a mile of beachfront and almost 20 miles of trail to explore.

At only 22 miles in length, the North Landing River packs a mighty punch of an astounding array of unique tidal habitats. This blackwater river is recognized as a biodiversity hotspot in Virginia and supports a greater diversity of rare plants and animals than any other place east of the Blue Ridge Mountains. Established in 1938, Back Bay National Wildlife Refuge is an 8,000-acre refuge tucked away in Virginia’s southeastern corner. It is located on a narrow peninsula that fronts the Atlantic Ocean to the east and Back Bay to the west. False Cape State Park lies on the southern edge of the refuge. A network of boardwalks, sandy paths, and waterways offers numerous ways to explore the amazing landscape and wildlife of this area. The 111,000-acre Great Dismal Swamp National Wildlife Refuge, including the 3,100 acre Lake Drummond, is a wilderness with a beauty that astounds and amazes. The black tannic water of the swamp is shallow and unusually pure and sterile, its acidity prohibiting bacteria growth. Many ship captains, including Blackbeard the Pirate, used to fill their kegs with the lake water because it would stay fresh during long sea voyages. The Blackwater River offers swamp paddling, miles of solitude, 800-year-old bald cypress trees, and longnose gar that can grow up to five feet in length. The list goes on and on, but you get the idea -- Virginia’s historical coast is a unique and special place that does not disappoint the visitor.


Day 1: We will meet at our lodging at noon. We will have a light lunch, make introductions, and assign cabins. After getting everyone geared up and giving paddling instruction, we will hit the water and embark on our first kayak trip of the week, a short two- to three-hour paddle.

Days 2-6: Each day we will usually combine kayaking for three to six hours (including lunch and breaks) with sightseeing and/or hiking for a couple of hours. We will carpool/caravan to our destinations and we will need volunteer drivers in order to do this. Drive times will be 30-60 minutes. A typical day will be group activities from 9 a.m. to 5 p.m., followed by dinner and then free time in the evening. Evenings will be reserved for optional hikes and/or beachcombing, with opportunities for fishing and bike riding. Wednesday will be an “off” day, when you will have the day to spend as you wish, exploring the area or just relaxing. We will try to kayak and explore as many of the following places as possible on this outing:

  • First Landing State Park
  • Chesapeake Bay Bridge Tunnel
  • Great Dismal Swamp NWR
  • Chesapeake Bay Beach
  • Back Bay NWR
  • False Cape State Park
  • Blackwater River
  • Cape Henry Lighthouse
  • Northwest River
  • First Landing Cross
  • West Neck Creek
  • Old Coast Guard Station
  • North Bay Loop
  • Francis Land House
  • York River State Park
  • Captain John Smith Chesapeake National Historic Trail
  • Virginia Beach Boardwalk and Pier
  • Virginia’s Eastern Shore

Day 7: Once we've eaten breakfast and packed up, we will say goodbye to new friends after having spent an amazing week of kayaking and exploring Virginia’s historical coast. Nearby historical Jamestown and Yorktown, as well as other numerous attractions, are available for those wishing to spend a few extra days of exploring.



Getting There

Norfolk, Virginia has the closest airport to our lodging at First Landing State Park. Washington D.C. or Baltimore, MD have larger airports and may offer you better airfares, but they are a three-hour drive to our lodging. Directions will be provided and a group roster will be sent to all participants several months in advance of the outing. We encourage carpooling to/from the outing and we will carpool/caravan to our various destinations throughout the week. We will need volunteer drivers and you may be asked to give/get a ride with someone to minimize the number of vehicles we use each day.

Accommodations and Food

We will spend six nights in cozy state park cabins at First Landing State Park in Virginia Beach, Virginia. Miles of hiking trails and Chesapeake Bay beach are nearby within the park. Most people find the cottages surprisingly nice, as they have most modern amenities. Participants will share rooms and couples will room together. Participants will take turns helping the leaders prepare meals and clean up. The first meal will be dinner on day one of the outing, and the last meal will be breakfast on day seven. We will go out to dinner once during the week -- this dinner is NOT INCLUDED in the trip price.

Trip Difficulty

We will paddle intermediate routes, averaging 6-12 miles and 3-6 hours on the water each day. You should be comfortable sitting in a kayak for up to 3-4 hours at a time. You need not be an expert paddler, but you should have previous kayaking experience. Basic paddling and safety instructions will be given on the first day of the outing. Hikes will be 1-5 miles in distance and on level terrain or sandy beaches. Each participant should understand that this is a group outing and that he/she will be required to stay with the group while we are on the water or trail. You should be flexible as plans and itineraries often change due to tides, weather, water levels, group ability, or other unforeseen reasons. We will carpool/ caravan to our various destinations throughout the week. Drive times vary from 30-60 minutes. Due to limited parking at some of the destinations, you may be asked to give or get a ride in order to minimize the number of vehicles that we take.

Note: Please be aware that ticks, poison ivy, and the occasional snake are all possibilities in this area.

Equipment and Clothing

We will provide a rental kayak, PFD/life jacket, and paddle to each participant. We will provide all group cooking gear. You will need to bring a reusable lunch container, water bottles(s), and a dry bag(s) to use throughout the week. A daypack will also be useful and you will need to have a personal first-aid kit. We will need volunteer drivers with vehicles as we will carpool throughout the week. A full gear list will be sent to all participants prior to the outing.


  • Winegar, Deane, Longstreet Highroad Guide to the Chesapeake Bay. RR Donnelley and Sons, 2000.
  • Gilbert, Lillie and Schufer, Vickie, Wild River Guide to Great Dismal Swamp Water TrailsECO Images, 2004.
  • Gilbert, Lillie and Schufer, Vickie, Wild River Guide to the North Landing River and its Tributaries. ECO Images, 2001.
  • Badger, Curtis, A Naturalist Guide to the Virginia Coast. University of Virginia Press, 2004.


The Chesapeake Bay covers 2,500 square miles and is North America’s largest estuary. An estuary is a partially enclosed area where the fresh water of rivers mixes with tidal salt water. If you decided to explore every cove and inlet of Chesapeake Bay, tracing the shoreline around the bay, you would end up traveling roughly 4,000 miles! Rain falls over a roughly 64,000 square mile area known as the Chesapeake Bay Watershed. Included in this watershed are 15 million people and 6 states. The Chesapeake Bay Foundation releases an annual report that describes the state of the bay each year. Using a baseline of 100 to describe the bay as it was observed by early explorers in the 1600s, the state of the bay is rated 1-100. An all time low of 23 was recorded in 1983. This number improved to 28 in 2000 and 32 in 2012. Although this trend shows improvement, the bay’s health is still rated as poor. Monitoring and continuous effort must be made in order for the bay to have a chance to continue to recover. We will experience the beauty of the Chesapeake Bay up close and discuss the mounting pressures on the health of the bay. These pressures include: urban sprawl and growth in the watershed, increasing human population around the bay, and the continued loss of wetlands, forests, and open space that buffer the bay’s waters. If we fail to change the way that we currently do things, losing the Chesapeake Bay is a real possibility. 

In 2014 America celebrates the 50th anniversary of the Wilderness Act. The Sierra Club, various other organizations with a wilderness focus, and the four federal wilderness management agencies are vigorously planning this celebration. The goal of the effort is to assure that a broader public knows about the concept and benefits of wilderness. Sierra Club Outings is a vital part of the celebrations for wilderness.

While the Act was far in the future when our outings program started, we were already promoting the principle behind it: to forever set aside from human developments certain special places, by civic agreement. This is the basic principle on which the Sierra Club was founded. The wilderness anniversary gives us an opportunity to highlight our organization’s leading role—in publicizing this principle, in passing the 1964 Act, and in achieving more designated wilderness since then.

Sierra Club National Outings is an equal-opportunity provider and will operate under permits from Great Dismal Swamp and Back Bay National Wildlife Refuges.



John Kovacevic has led and co-led many Sierra Club Outings since completing an Outdoor Leadership Training Course in 2004. He is certified as a Wilderness First Responder, and completed both ACA kayak instructor certification courses as well as several water rescue courses. John’s current focus is on kayak trips in the Southeast, with South Carolina, Coastal Georgia, and Florida being like second homes and favorite paddling destinations. John looks forward to sharing some amazing places with you that he has explored and discovered, as well as finding some new ones. After adding cozy and comfortable lodging in scenic locations and great meals to the mix, you’ll enjoy the trip of a lifetime!

Assistant Leader:

Hiking, biking, kayaking, and backpacking, Russ Norfleet loves to explore beautiful wild and scenic places with other adventuresome souls. He is a Sierra Club local and inner city outings leader (Washington, DC) and a professional tour guide (east coast U.S.), passionate about connecting young people and adults with the country’s natural, historic, and cultural treasures.

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