Urbanna Kayak Trail

Paddle Through History

Embark on the Urbanna Kayak Trail Tour, a unique aquatic journey that combines the serene beauty of Urbanna Creek with a fascinating exploration of the area's historic sites. This guided loop offers a fresh perspective on the creek’s scenic surroundings and rich heritage, allowing you to paddle through history and nature in one captivating experience. Ideal for adventurers and history enthusiasts alike, the Urbanna Kayak Trail Tour is a perfect way to discover the stories and landscapes that make this region truly special.

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Stops On This Trail

1. H.S. Chowning Co.

Near this site H. S. Chowning & Co. owned a cement manufacturing plant that made concrete building blocks and well curving. There was a pier out in the creek for unloading sand and cement delivered to the plant by boat. Huge barges were towed across the river to collect tons of white sand that was off-loaded by wheelbarrows when brought back to Urbanna. Cement blocks were hauled from the plant on Chesapeake Bay sail powered schooners and motorized deck boats and delivered throughout the region. There was a six-inch pipe free-flowing artesian well on the site used to make the blocks. During and long after the plant closed, town children using the public beach wore a path to the well to use the cool flowing water that contained a bit of sulfur in it to sooth the pain from stinging nettles. If beach sand rubbed across the hurt did not relieve the pain, a race to the well was the next relief step – and look out for those sand briars! Also near this site was a cotton gin. The cotton gin building was made of galvanized corrugated sheet metal and was two stories high. There was Fordson tractor powered device used to separate seed from cotton and a large mechanical press used to bale the cotton. Pre-World War II, town children recalled that when the cotton gin was not in operation, they would jump from the inside second floor level into the large pen that held clean and un-baled cotton. When the plant closed, the press was moved to Barnhardt Duck Farms, once located a couple miles outside of town and was used to bail duck feathers.

Along this beach shore was the staging area for the Urbanna Labor Day Boat Races. The annual races were held on Urbanna Creek from 1940 to 1966. Outboard and inboard hydroplane boats raced for cash and trophies. Outboard races were on Saturday and inboard races on Sunday. The American Powerboat Association (APA) for years warned that the racecourse was too short and was dangerous. Finally, the APA sanction for inboard races was revoked in 1966. The races were sponsored by the Urbanna Booster’s Club and Middlesex Lions Club. The organizers held the outboard races in 1966 but opted to stop the event in 1967. During the early years, there was a beauty pageant and a yacht parade with decorated boats. One year a boat was decorated with a large swan that was carrying the queen of the races and her court. Another year there was a staged battle between replicas of the Merrimac and Monitor. Blanks were fired from canons and firecrackers were shot off to give the effect of gunfire. For most of the years, the racecourse was located on the eastern side of the bridge but for a few years races were held on the western side of the bridge. The bridge was closed to automobile traffic and loaded with spectators from one end to the other watching and cheering the races.

At the turn of the 20th century, Standard Oil Co. had a bulk storage plant at this site. It was later known as Urbanna ESSO bulk plant. As an ESSO plant it was managed by J. T. Thrift starting in 1922 and oil was delivered by oil barges until 1965 when trucking took over the business. Prior to barges, gasoline and oil were delivered in barrels on sailing schooners. The Standard Oil Dock had also been used as a steamboat wharf and prior to being called Standard Oil Dock it was named Gressitt and Yates Wharf and later, Gressitt’s Wharf. Jno. D. Gressitt ran a general merchandise store near the site and was a “planter and shipper of shell oysters and agent for Standard Oil Co.” as was detailed on one of Gressitt’s invoices dated March 9, 1910. The wharf was later run in the 1960s by Beryl “Dick” Newman (a Medal of Honor recipient in World War II). The concrete bridge across Urbanna Creek today is named in his honor. 

During colonial times, Jamison’s Cove had enough water depth for ocean going sailing craft to moor. English ships came annually bringing supplies to town merchants and residents originally from Scotland and England. Ships were able then to get up in the cove to offload supplies and load hogheads of tobacco. The waters just south of the entrance to Jamison Cove entrance was used by oyster grower Russell Davis as state leased private oyster grounds. During times when the creek and river were frozen solid, Davis kept a large supply oysters on these grounds. During long freezes he had his crew punch holes in the ice and while standing on the ice, would tong up oysters. They would gather the bushels needed to supply his customers when all other growers were stuck in the ice. During these times, he kept a man on shore 24-hours a day with a shotgun to discourage any thievery.

This was the site of the ferry landing between Irvington and Urbanna. Beginning on May 15, 1924, a private ferry named Frances B. Garrett ran three days a week across the Rappahannock River. Prior to this, a colonial ferry had operated for many years that came from directly across the Rappahannock River to Urbanna. It was known as Chowning’s Ferry. Ferries ran across the river at different locations in the county until the Robert O. Norris Bridge opened at Grey’s Point on August 30, 1957, connecting Lancaster and Middlesex counties.

Over the years many businesses were located on this site that today houses Oyster Harbor Condominiums. J. W. Hurley and Son Seafood ran a general merchandize store on this site and were packers of “oysters and fruit.” Hurleys’ oyster shucking house was one of the largest in the region with over 50 shuckers working in the plant at a time. The famous “Boyd’s Favorite Urbanna Brand Tomatoes” were canned in the nearby Hurley tomato packing plant. Later, they opened Hurley’s Hotel and Restaurant that was noted for serving fresh caught fish and crabs. The restaurant was later demolished to make way for Norris Granary later known as Southern States Granary elevators that held, corn, wheat and soybeans purchased from local farmers and hauled to large facilities in Norfolk and Salisbury, Md. Town boys of the 1960s can remember shaky and “don’t look down” midnight climbs to the top of the elevators to collect pigeon eggs from nests to hatch out in homemade incubators and to grow the birds to complete their Boy Scout bird study merit badges. Before the granary the town’s ice plant was located here. The plant made block ice weighing 300 pounds (a standard size for commercial ice). It was sold locally to seafood packers and was also delivered house-to-house in town in a wheelbarrow. John Street who lived on Watling Street delivered ice via wheelbarrow and had a scale and ice pick to chip the ice off the block. He was noted for allowing small children of the town to ride atop the ice as he pushed the wheelbarrow down the street. The plant was owned by a Mr. Kennard who hauled ice to steamboat wharves up and down the Rappahannock River in his ice boat named Drannek (Kennard spelled backwards). The plant was loud as it was run by a single cylinder Diesel engine with a flywheel, eight or nine feet in diameter and it made a “great big’ popping noie when it was pulling the compressor to make ice. Another business near this location was Powell’s Mill. The mill was a two-story frame building used to supply flour and cornmeal to customers. It was originally Rosegill Patent Roller Mill, which made “high-grade flour and meal, shorts, chop and bran.” That mill was originally located on Rosegill millpond outside of Urbanna. The Rosegill mill building, along with the patent rollers, were moved in 1909 to this location and traded as the Middlesex Manufacturing Co., advertising “the finest patent roller mill in the area.” The name of the mill was later changed to Powell’s Mill. “Powell’s Pride Flour” was the chief product.

Over the years many businesses were located on this site that today houses Oyster Harbor Condominiums. J. W. Hurley and Son Seafood ran a general merchandize store on this site and were packers of “oysters and fruit.” Hurleys’ oyster shucking house was one of the largest in the region with over 50 shuckers working in the plant at a time. The famous “Boyd’s Favorite Urbanna Brand Tomatoes” were canned in the nearby Hurley tomato packing plant. Later, they opened Hurley’s Hotel and Restaurant that was noted for serving fresh caught fish and crabs. The restaurant was later demolished to make way for Norris Granary later known as Southern States Granary elevators that held, corn, wheat and soybeans purchased from local farmers and hauled to large facilities in Norfolk and Salisbury, Md. Town boys of the 1960s can remember shaky and “don’t look down” midnight climbs to the top of the elevators to collect pigeon eggs from nests to hatch out in homemade incubators and to grow the birds to complete their Boy Scout bird study merit badges. Before the granary the town’s ice plant was located here. The plant made block ice weighing 300 pounds (a standard size for commercial ice). It was sold locally to seafood packers and was also delivered house-to-house in town in a wheelbarrow. John Street who lived on Watling Street delivered ice via wheelbarrow and had a scale and ice pick to chip the ice off the block. He was noted for allowing small children of the town to ride atop the ice as he pushed the wheelbarrow down the street. The plant was owned by a Mr. Kennard who hauled ice to steamboat wharves up and down the Rappahannock River in his ice boat named Drannek (Kennard spelled backwards). The plant was loud as it was run by a single cylinder Diesel engine with a flywheel, eight or nine feet in diameter and it made a “great big’ popping noie when it was pulling the compressor to make ice. Another business near this location was Powell’s Mill. The mill was a two-story frame building used to supply flour and cornmeal to customers. It was originally Rosegill Patent Roller Mill, which made “high-grade flour and meal, shorts, chop and bran.” That mill was originally located on Rosegill millpond outside of Urbanna. The Rosegill mill building, along with the patent rollers, were moved in 1909 to this location and traded as the Middlesex Manufacturing Co., advertising “the finest patent roller mill in the area.” The name of the mill was later changed to Powell’s Mill. “Powell’s Pride Flour” was the chief product.

The Tides Inn, a luxury hotel in Irvington in Lancaster County, opened in 1947. Lancaster was a dry county (alcohol free). However, because private clubs were not bound by the same constraints, the Tides owner formed the Chesapeake Club. Middlesex County was a wet county, so the Inn purchased a yacht that made Saturday runs across the river to Urbanna’s liquor store. It was known as the “whiskey run.” Sun Tan IV was an early yacht used by Tides Inn to make the trip but the most famous was the Miss Ann. The Miss Ann was built in 1924 for a Detroit banker, industrialist and yacht collector. Tides Inn purchased the Miss Ann in 1952 and completely refurbished the boat. The refurbishing took four years so in 1956 she started making the whiskey run to Urbanna. When she came to town on Saturdays, she moored at this site.

Southside Marine Railway was a railway and boating business started in 1915 by Walter Cary Palmer and Newton Weaver. It featured a railway, machine shop, and boat repair facility. Dodge automobiles and Graham Trucks were once sold there as well. The marine railway provided work for local boat repairmen. The Dodge agency folded as other car dealership came to the town and county but the boating part survived for many years. The marina was purchased by Ben Hurley in the 1940s. Hurley added covered boat slips and modernized the facility. The railway was removed in the late 1950s and replaced with a Travel-lift, which then was only the second of its kind located in the state of Virginia. Southside Marine Inc. was the first full-service marina in the area and was a model for all marinas that were to come in Middlesex County.

At this location Dixie Pickling Co. built a pickle factory in the creek. It was later owned by Borshay Pickling company, On January 31, 1916, the Urbanna Board of Trade pledged $92 to encourage the firm to locate in Urbanna. Captain D. M. Nelson and Messrs. Green & Bristow agreed to give 1000 bushels of oyster shells toward the foundation of the pickle house building. The company came to Urbanna and built out in the water on the shoreline at this site. Next to the pickle house, Columbus (Captain Lum) Simon Burton, born in 1845 had a pier with a building on the end near the pickle house. He ran a seasonal business making shaft tongs for oystermen who came to Urbanna during the annual Rappahannock River wintertime oyster tong season. Capt. Lum’s 1898 logbook showed that he sold 105 tong shafts that he made out of ash, fir, and pine wood. He grossed $344.25 from August to December. In the summer he would purchase, and repair old sail powered log canoes to sell to boost his yearly income. According to his 1897 logbook, he sold a rebuilt log canoe for $75. In the warm weather months, Capt. Lum’s daughters used his pier to “chicken neck” for hard-shell crabs which were steamed and served for dinner at the Burton House. Capt. Lum and his wife, Lucy Hackney Burton ran a boarding house up on the hill where many return customers came annually just to get another taste of Lucy’s local cuisine. 

Jones and Baker Oyster Shucking House. Bill Jones and Boxley Baker operated an oyster shucking house near this site in the 1940s.

Burton’s Steamboat Wharf was run by the steamboat agent Aubrey Burton and named Burton’s Wharf for Aubrey’s father Columbus (Lum) Burton. The wharf was originally called Palmer’s Wharf as Alfred Palmer was owner and dock-master from the 1840s until the Burton’s purchased the wharf about 1880. Local canneries, farmers and merchants received and shipped their goods from the wharf to markets in Baltimore, Norfolk and Fredericksburg via steamboat. Passengers bound for any location in Tidewater Virginia and Maryland could book a state room and even arrange for their cars to accompany them aboard the steamers. At this site, the James Adam Floating Theater came each summer to town and moored in this spot. It was an annual event in town from 1915 until it burned in 1941. After being towed from the last river town at which it played, it would arrive in Urbanna on a Sunday afternoon. There was great excitement among the town’s young people when the theater could be seen on the horizon. It was built on top of a barge and towed by two tugboat, Elk and Trouper. The Trouper was the largest tug and used to tow, while the Elk was used more in the docking process. The captain of the Elk was Will Canon of Urbanna. Town youngsters did odd jobs for the theater and were rewarded with free $.35 passes for evening shows. Charlie Hunter and Beulah Adams were theater stars and in 1926 Edna Ferber wrote the novel Show Boat based on her experience with the James Adams Floating Theater. 

The broom factory was a single-story cement block building with oyster shells around the perimeter. The business was owned and operated by R. O. and Ed Smith of Saluda. It closed about 1930.

The Swirley Top was built by Mr. and Mrs. A. H. Henkel in 1950. This was the first fast food takeout business in town. The business had a small building beside the main one for playing pool and sitting around. The business was later run by Catherine Payne Via and under her ownership the best banana milkshakes “in the world” could be purchased. When Urbanna Bridge was moved away from the foot of Watling Street in 1957 to its current site, the business continued to operate for a number of years but closed in the mid-1960s as traffic waned with the change in the road. 

The River Rink was built in the 1930s out over the water atop oak pilings and was a two-story structure. The first story contained a skating rink, snack bar, lounge, and had pinball and slot machines. The second story had a bowling alley and rooms for the owner and employees to live. The River Rink burned in 1947. 

On August 7, 1858, the Urbanna Toll Bridge Company was formed with the sole purpose of building a wooden bridge across Urbanna Creek. The bridge entered Urbanna at this site. This private company was formed to build the bridge to offset efforts by the county to move commerce to more centralized locations elsewhere in the county. Through the 1849 referendum, county voters removed the county seat from Urbanna and moved it to Saluda. The first bridge was completed in 1859 and was one lane with room in the center of the bridge for two cars to pass. The 1859 bridge was replaced with a new bridge in 1910. That bridge was replaced with a two-lane bridge in 1926 and in 1928 Urbanna Bridge was taken into the Virginia Highway System. The concrete bridge across the creek today was built in 1957.
Located near where Bridge Marina’s sales building was Thornton’s Store. It was one of just a few businesses in town owned by an African American. Washington (Wash) Thornton owned the general merchandise store and barber shop and that his father had run it before him. Wash was the Urbanna Bridge draw span operator for many years too as his business was right next to the bridge. His store clientele was mostly African American. He allowed Black oystermen to moor their oyster boats along his shoreline and many boats were left there to die. The bones of several log canoes are buried in the mud below what is today Urbanna Bridge marina. The store was torn down to build the marina.

The waters of Urbanna Creek have provided a livelihood for generations of watermen. Since man first laid eyes on Chesapeake Bay, we have looked to it for food and nourishment. When the Baptist movement first began in the early 1700s, new members of the denomination looked to the creeks and streams to provide a spiritual type of nourishment. This location was the annual baptismal spot for members of the all-Black Lebanon Baptist Church founded in 1891 and once located just outside of Urbanna on Old Virginia Street. Usually once a year, Blacks congregated on the hill leading down to the bridge and creek water to be baptized. Cars were lined up on both sides of the road up to Rosegill hill. When signaled a long line of children and adults dressed in white ropes would walk single file down to the creek. After some preaching and sweet gospel music, they were immersed in the water as an expression of their faith in Jesus Christ. On the other side of the creek, white children sitting on the hillside watched with interest and, for the most part, with reverence. 

Barn Landing was on Rosegill Farm and used as a schooner and deck boat landing for the hauling and delivery of bulk freight – lumber, fertilizer, coal, watermelons, and other bulk commodities.  

Several yards from the site of Barn Landing are the bones of the Kate H. Tighlman, a two-mast sailing schooner. After World War II, with the decline of the schooner era and rise of overland trucking, the vessel was beached and left to die on Rosegill shore. The boat was owned by sea captain R. O. Smith Sr. who lived on Oakes Landing Road near Saluda. The centerboard trunk and rips of the vessel could still be seen in the shallows into the 2020s. 

In the summer of 1863 along the Rosegill path leading down to the boathouse John Taylor Wood, nephew to Confederate president Jefferson Davis, launched a series of naval attacks and used Urbanna Creek as his staging grounds. After the capture of two Union vessels, the Rosegill home was used as a makeshift hospital to care for Confederate, and captured Union and former enslaved troops. When it was implied that the Black troops would not be treated, mistress and owner of Rosegill Eliza Bailey, (originally from New York State) made it clear that all would be treated in her house – or none.

Round smooth ballast stones once used to define walkways and gardens in the Town of Urbanna are a reminder of the colonial shipping business that was so much a part of the town’s economy. Near this site in several feet of water are piles of ballast stones that were thrown overboard from colonial ships. The ballast was thrown into the creek and replaced with hogshead of tobacco weighing a thousand pounds each.

Bailey Point was named for Capt. John Bailey of Rosegill. There was an old pine tree on this point used for over 100 years as a gallows tree. During colonial days the tree was used to hang pirates or their body parts as reminders to those willing to break laws that there was swift and definitive justice in Urbanna and throughout the Virginia colony. The tree was used as a hanging tree into the 19th century when Urbanna was the county seat of Middlesex County. The town was the Middlesex County seat (1748 to 1853). The tree was visible from the river and creek and people came down to the water’s edge and watched from boats to witness the hangings. The tree was still standing into the 1930s and referred to then by locals as the gallows tree.

From the beginning of the Town of Urbanna’s public beach in the 1940s an Urbanna lad came of age when he was able to swim across the creek to Rosegill beach and back to the town beach. The lure of this private property site brings many people to its sand and is used by generations of boaters and swimmers thanks to the generosity of past and present owners of Rosegill. PHOTO 1: The buyboat East Hampton of Chestertown, Maryland passes-by Rosegill Beach at a recent Chesapeake Bay Buyboat Association Rendezvous at the Urbanna Town Marina. (Courtesy of Larry Chowning)

Originally there was an island sandbar on the west side of the entrance to Urbanna Creek. After the Civil War, Jimmy Chandler homesteaded the spit by building a small shack up on pilings out on the sandbar. Later, as sand filled in and connected the land to Urbanna, three cottages were built on the spit. The cottages were owned by Mrs. Arthur Chapman, Lewis Kucion and Dr. W. P. Jones. A stone jetty was built in the late 1880s to discourage upriver sand from filling in the channel and to collecting along the spit. Several other cottages were built there over time but only one of the original cottages is standing today. With the introduction of central sewage in the 1960s, landowners agreed to become part of the incorporated Town of Urbanna. Today, some of the finest homes in town are on the island, as some locals still call the land today. 

Donaldson’s Steamboat Wharf extended out into the creek at this location and the old shirt factory stood on the high ground above the bend in the creek. The business founded as the Urbanna Manufacturing Plant in 1902 made overalls and work shirts and was later converted to the Urbanna Beach Hotel. There was a pavilion on the shore below the hotel and music with live bands and dances were held there. When live music was not available there was a jukebox and young and old enjoyed themselves there at very little expense. A pier extended into the creek and visitors came regularly by boat. Later, the old hotel was purchased by C. D. Dameron who operated it as the Urbanna Lodge and Motel into the 1970s. Dameron built the first swimming pool in town in the early 1960s. Although the old shirt factory building has been demolished the swimming pool is still there as part of Queen Anne’s Cove Condominiums.

The Urbanna town swimming beach was located at this site. The beach was wide and sandy. Pilings were installed enclosing the swimming area and fish net was attached to the pilings to keep stinging nettles out. Later on, frames with small mesh wire were used to accomplish the same effect. A pier with a diving board complimented this activity. Many children learned to swim here under the direction of Mr. Bill Jones whose patience extended but so far. When a child was ready to swim but still had doubts, Mr. Jones method of learning was “sink or swim.” Many a lad was thrown into deepwater by Mr. Jones with those instructions. No one ever drowned! The beach land was privately owned by the owners of “Terrapin Hill” and leased by the town for a dollar a year. 

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