The beach at Point Lookout State Park.

An Outdoor Odyssey: Off the Grid Island Getaway on The Chesapeake Bay

The beach at Point Lookout State Park.
 

Ridge to Ewell on Smith Island, 59 miles plus a ferry trip, 6 days / 5 nights

Kayaks for use of Pier 450 Guests

Kayaks for use of Pier 450 Guests

Dockside  Dinner at POV Restaurant at Pier 450 Motel
@thehoneymoonist

Dockside Dinner at POV Restaurant at Pier 450 Motel

Day 1 - Soak Up the Peaceful Paradise

Ridge
  • Drive to Ridge 
  • Bring provisions for breakfasts and snacks
  • Check in at the Pier 450 Motel, a boutique roadside-esque motel housed in a transformed 1940s-era fishing camp
  • Savor Chesapeake flavors during dinner at POV Restaurant and enjoy a made-from-scratch, locally sourced culinary adventure.
  • Relax and rest up for next day’s adventures

: Captain Phil Langley of Fish the Bay Charters describes crab ecology and crabbing.

Captain Phil Langley of Fish the Bay Charters describes crab ecology and crabbing

Capt. Phil Langley cooks up steamed crabs during the Hook and Cook program from Fish the Bay Charters

Capt. Phil Langley cooks up steamed crabs during the Hook and Cook program from Fish the Bay Charters

Day 2 - Live the Watermen’s Life - Cook Your Catch 

Ridge
  • Be up bright and early for a Watermen’s Heritage Tour with Chesapeake Bay Storyteller Fish the Bay Charters, and try your hand at crabbing and living the watermen’s life
  • Cook your catch and have a crab feast when you return
  • Relax during a lazy afternoon with a water view in an adirondack chair on the lawn at Pier 450 Motel OR paddle a loaner kayak from the motel on Smith Creek
  • Head to dinner at the SALT Waterfront Kitchen with great views of the Smith Creek and a fresh creative menu
  • Spend another night luxuriating in beach-chic hospitality at Pier 450 Motel

 

Point Lookout Lighthouse

Point Lookout Lighthouse

Sunset on the fishing pier at Point Lookout State Park.

Sunset on the fishing pier at Point Lookout State Park

Fishing at Point Lookout State Park

Fishing at Point Lookout State Park

Day 3 - See Land’s End

Ridge to Scotland
  • Enjoy your morning coffee on the Pier 450 Lawn
  • Pack a picnic lunch with provisions from the Food Lion in Ridge
  • Travel to Point Lookout State Park (14 minutes travel time)
  • Rent a canoe at the campground and paddle a water trail
  • OR Fish from the Point Lookout Pier
  • Hike the Trails at Point Lookout State Park
  • Enjoy a picnic lunch on the beach
  • Walk the Beach and swim in the Chesapeake Bay - or relax with expansive Bay views
  • See the Point Lookout Lighthouse and Civil War Museum
  • Return to Ridge for dinner at POV Restaurant at Pier 450. It’s so delicious that you’ll want more!
  • Return to your cozy room at Pier 450 Motel

 

The Pelican Tour with Experience Smith Island, LLC

The Pelican Tour with Corbin Tours

The Pelican Tour with Experience Smith Island, LLC

The Pelican Tour with Corbin Tours

Smith Island Cultural Center
Sherri Marsh Johns

Smith Island Cultural Center

Bayside Inn Restaurant, Smith Island

Bayside Inn Restaurant, Smith Island

Day 4 - Get Off the Beaten Path 

Ridge to Ewell, Smith Island

  • Drive to the Point Lookout Marina 
  • Catch the Ferry on foot from the Point Lookout Marina to Ewell on Smith Island (10 a.m. departure Thurs. - Sun. seasonally)
  • Eat lunch at Smith Island’s Bayside Inn to sample local seafood favorites
  • See the astounding natural wonder of the Pelican Rookery on a boat tour with Corbin Tours
  • Tour the Smith Island Cultural Center 
  • Settle in for the evening at the Smith Island Inn and enjoy a catered dinner
  • Feel the tranquility, smell the salty air, hear nature’s music and stargaze

 

Welcome to Tylerton on Smith Island

Welcome to Tylerton on Smith Island

: Smith Island Cake
Somerset County Tourism

Smith Island Cake

Day 5 - Set Your Clock to Island Time

Ewell and Tylerton on Smith Island to Point Lookout and Piney Point
  • Rise before daybreak and join a waterman for a crabbing trip with Smith Island Eco Tours and Charters
  • OR Wake to the sunrise and the sounds of watermen at work
  • Enjoy Breakfast at the Inn (included)
  • Paddle the Smith Island Water Trails through the Martin National Wildlife Refuge from Ewell to Tylerton (2.25 miles of paddling one way; kayaks, canoes and life jackets are available to borrow from Smith Island Inn)
  • Walk to Drum Point Market to pick up lunch in Tylerton and explore the town
  • Paddle back to Ewell (2.25 miles of paddling)
  • Visit the Smith Island Bakery for their famously delicious Smith Island Cake
  • Take the ferry from Smith Island to Point Lookout (4:30 p.m. Thurs. - Sun.)
  • Drive to Piney Point (35 minutes)
  • Reflect on your experience of the “Island Out of Time” over dinner at the Ruddy Duck Seafood and Ale House in Piney Point 
  • Stay the night at the Island Inn & Suites, a boutique hotel with gorgeous water views on the St. Mary’s River

 

Piney Point Lighthouse

Piney Point Lighthouse

Sunrise at Piney Point Beach
@aeoshiro

Sunrise at Piney Point Beach

Day 6 - Discover Lighthouse Legends

  • Enjoy breakfast from your own balcony and take in gorgeous river views
  • Explore the scenic Piney Point Lighthouse Museum & Historic Park just down the road from the inn
  • Dip your toes in the water at Piney Point Beach for your last splash before returning home

This trip can be joined to trip Option 1 to extend your "baycation."

 

Maryland's Great Chesapeake Bay Loop Getaway Guide

Find a treasure trove of ways to explore the Bay, and meet our skilled Chesapeake Bay Storytellers.

Download Guide