Routes & Towns

Epiphany’s home base is in St. Michaels, Maryland, where most charters will last 3 hours from start to end in the town of St. Michaels. However, trips can be started from alternate locations for an additional fee. Routes are flexible and can be custom planned for your group. Below is a map of some popular towns perfect for visiting by boat. Following the map are some descriptions of each town, some of our favorite places to visit, and a list of activities we love to do.

St. Michaels

  • Quaint, historic town with a beautiful harbor, exceptional dining, and one of a kind shopping
  • Voted as a top 10 best small coastal town by USA Today
  • Known as the town that fooled the British by placing lanterns high on the masts of sailboats at the tops of trees causing the British to overshoot the town
  • Tourism site with attractions, restaurants, and shopping information
  • Our favorite spots: Foxy’s Harbor Grille, Justine’s Ice Cream Parlor, Ava’s Pizzeria & Wine Bar, Theo’s Steakhouse, Chesapeake Bay Maritime Museum
  • Activities: Take a 2 hour sailing cruise on historic, luxury Selina II, rent a bike, kayak or paddle board from Shore Peddle & Paddle, walk down the main S. Talbot Street for great shopping and sight seeing, walk through the Chesapeake Bay Maritime Museum to see several historic boats and climb to the top of a lighthouse for a wonderful view, visit one of many playgrounds, eat steamed blue crabs at The Crab Claw

Oxford

  • Charming, tree lined and waterbound village with a population of less than 1,000
  • One of the oldest towns in America
  • Long history in maritime activities
  • Sailboats arrive from all over the bay to dine at various local restaurants
  • Tourism website with more information
  • Our favorites spots: Scottish Highland Creamery, Oxford Park, Robert Morris Inn Restaurant, Capsize, Doc’s Sunset Grille
  • Activities: Ride the Oxford-Bellevue Ferry, rent a bike, paddle board, jet ski or kayak from Dockside Boat Rentals on 104 W. Pier Street, have a picnic at scenic and shady Oxford Park, enjoy ice cream waterside at Scottish Highland Creamery, visit sandy Oxford Beach for a swim or some sun bathing

Cambridge

  • Located on the broad Choptank River
  • Dates back to 1684 making it one of the oldest colonial cities in the state
  • Rich maritime heritage that can be explored in museums, through historic district tours and river cruises
  • High Street has been called one of the the most beautiful streets in America by Author James Michener in his novel Chesapeake
  • Many of the gracious homes on High Street date from the 1700’s and 1800’s
  • Downtown tourism website with more information
  • Our favorite spots: RAR Brewing, The Wine Bar, Black Water Bakery, The High Spot Gastropub, Stoked Wood Fired Eatery
  • Activities: Check out the Choptank River Lighthouse, walk down High Street for shopping and restaurants, take a historic tour, visit Sailwinds Park and walk under the Choptank River Bridge

Tilghman Island

Kent Island

  • The largest island on the Chesapeake Bay
  • The Chesapeake Bay Bridge connects Kent Island to the western shore
  • The island is just barely separated from Maryland’s eastern shore by the Kent Narrows channel
  • Before the Chesapeake Bay Bridge opened in 1952, the area served as hub for ferry service and steamboat travel between the eastern and western shores
  • Tourism website with additional information
  • Our favorite spots: The Jetty Dock Bar, Bridges Restaurant, Knoxie’s Table, Rustico Restaurant & Wine Bar
  • Activities: Visit the Chesapeake Exploration Center, eat steamed blue crabs at Harris Crab House, listen to live music at one of the many bayside restaurants, visit Matapeake Beach for swimming or walking the trails and pier, look for the Bloody Point Bar lighthouse just south of the island, visit Terrapin Beach Nature Park to walk the trail and view two observation blinds

Chesapeake Beach

  • Quaint, historic bayside community with secluded beaches and waterfront restaurants
  • Founded by the Washington and Chesapeake Bay Railway Company in 1894 as a vacation destination for DC residents
  • Tourism website with additional information
  • Our favorite spots: Shopping at neighboring North Beach, Westlawn InnNeptune’s Seafood Pub, Herrington Harbour tiki bar and pool
  • Activities: Visit the Chesapeake Beach Railway Museum, enjoy the beach at public Bay Front Park, take the kids to the Chesapeake Beach Water Park with pools, slides and waterfalls, walk the Chesapeake Beach railway trail, visit neighboring North Beach to walk the boardwalk and do some shopping, dine at Westlawn Inn in a 1926 historic home with jazz nights, rent a slip at Herrington Harbour Marina and visit the pool and tiki bar, walk the public fishing pier at North Beach

Annapolis

Rock Hall

  • A quiet waterfront town nicknamed the “Pearl of the Chesapeake”
  • Many miles of shoreline, public docking and marinas
  • Home to the Eastern Neck National Wildlife Refuge, a 2,285 acre island that is habitat for thousands of waterfowl
  • Tourism website with more information
  • Our favorite spots: Waterman’s Crab House, Harbor Shack
  • Activities: Eat steamed blue crabs and listen to music at Waterman’s Crab House or Harbor Shack, stroll Main Street and do some antique shopping, dine at Osprey Point Inn, walk the trails of the Eastern Neck National Wildlife Refuge, swim in the pool at Haven Harbour Marina, listen to live music at the Community Gazebo

Chestertown

  • Located along the banks of the Chester River
  • Home of one of the old colleges in the country, Washington College
  • Full of historic homes, churches, and a variety of unique shops
  • The annual Downrigging Festival takes places in October and has evolved into one of the largest annual tall ship gatherings on the east coast. The Chester River becomes package with ships, schooners and wooden boats.
  • Tourism website with additional information
  • Our favorite spots: Evergreen Bread Company, Play It Again Sam, Fish Whistle
  • Activities: Visit 3,000 acre Chesapeake Farms Wildlife Habitat, stroll downtown and visit the shops along High Street, Taste some wine at Cassinelli Winery & Vineyards, dine next to the Chester River at Fish Whistle, catch the annual Downrigging Festival in October, visit the farmer’s market in Fountain Park
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