St. Michaels · Waterfront luxury
Inn at Perry Cabin
A luxury inn on the Miles River at the edge of St. Michaels, with gardens, a spa and Stars restaurant. The romantic splurge.
Official details for Inn at Perry CabinMaryland · Couples · Two nights
St. Michaels & Easton
Crabs, sailboats and a waterfront inn.
On Maryland’s Eastern Shore, the old harbor towns of St. Michaels and Oxford sit on quiet creeks off the Chesapeake Bay, with historic Easton a short drive inland. Stay at a waterfront inn, pick crabs on the harbor, ride the little Oxford ferry, and watch the sunset from the deck of a sailboat.
Waterfront innsChesapeake crabsMaritime history
YOUR ROUTEKMYR to KESN
STRAIGHT-LINE DISTANCE~337 NM
ILLUSTRATIVE FLIGHT TIME~2 hr 30 min
WEEKEND STYLETwo nights · Courtesy or rental car
Time illustration: direct distance at 150 KTAS plus 15 minutes for departure and arrival, matching the discovery page. Use ForeFlight for your actual flight plan.
01 / Aviation & getting around
Land in Easton, drive to the water.
KESN, Easton/Newnam Field, is a towered airport just north of Easton, about 20 minutes from St. Michaels and Oxford.
The FBO
Maryland Air · Easton/Newnam Field
410-822-040029137 Newnam Road, Suite 5, Easton, MD 21601
Directories list a courtesy car and rental cars at Maryland Air. Easton Jet Service (410-820-8770), also on the field, lists a rental car office on site. Ask about two-night parking and fees. No live fuel price is shown.
The Washington, DC SFRA lies across the Bay to the west, and Patuxent River and Dover have busy military airspace nearby. Review the sectional, restricted areas and current NOTAMs and TFRs.
02 / Where to stay
Choose your stretch of shoreline.
A celebrated waterfront inn, a grand historic hotel or a relaxed island hideaway. Rates and availability need travel dates.
Easton · Historic
The Tidewater Inn
A classic 1949 hotel with 86 rooms in the middle of Easton, home to Hunters’ Tavern and an easy walk to shops and the Avalon Theatre. The inn was listed for sale in 2026; confirm details when you book.
Official details for The Tidewater InnTilghman Island · Waterfront
The Wylder Hotel
A relaxed waterfront hotel in an 1898 boarding house on nine acres of Tilghman Island, about 15 minutes past St. Michaels, with Tickler’s Crab Shack and sunset views over the Bay.
Official details for The Wylder Hotel03 / Where to eat
Two dinners. One crab feast.
Blue crabs are the point from late spring to fall. Reserve weekend dinners.
Friday dinner · Easton
Bas Rouge
Refined contemporary European dining in an intimate room in downtown Easton. The special-occasion dinner.
Official details for Bas RougeSaturday dinner · Perry Cabin
Stars
Locally inspired cooking at Inn at Perry Cabin, inside or on the terrace overlooking the river. Go early for sunset.
Official details for StarsLunch · St. Michaels harbor
The Crab Claw
A St. Michaels institution on the harbor, where you pick steamed crabs at picnic tables by the water. Seasonal; check that it is open.
Official details for The Crab Claw04 / Things to do
Boats, a ferry and a lighthouse.
Slow and easy. Leave time to sit by the water.
Chesapeake Bay Maritime Museum
A waterfront campus in St. Michaels with the 1879 Hooper Strait Lighthouse, working boatyards and historic Bay boats. Allow two hours.
Museum informationThe Oxford–Bellevue Ferry
One of the oldest privately operated ferries in the country, crossing the Tred Avon River between Bellevue and Oxford. Ride it with bikes or the car for a loop to Oxford. Seasonal.
Ferry scheduleOxford
A tiny, quiet town of shaded streets, boatyards and a little beach on the Tred Avon. Lovely for a slow afternoon.
A sail on the Bay
Sunset sails and skipjack cruises leave from St. Michaels and Tilghman Island in season.
Downtown Easton
Brick sidewalks, galleries, the Academy Art Museum and the restored Avalon Theatre.
Optional / Spa & relaxation
The Spa at Perry Cabin · Time for two
The inn’s spa has a private couples suite, a steam room and a relaxation lounge with an outdoor terrace.
Booking: Ask about couples treatments, access for non-inn guests, current pricing and cancellation policy. No prices are shown here, and no appointment has been booked.
05 / What’s happening
Sometimes the season is the reason to fly.
This prototype links to the county visitor site. It does not yet match events to your travel dates.
November
Waterfowl Festival
Easton’s big wildlife art and decoy festival, usually the second weekend of November. Fun and busy; book early.
July
Plein Air Easton
One of the country’s largest outdoor painting competitions, with artists painting all over town.
May–October
Crab and sailing season
The best months for crabs, sails and waterfront dining. Summer is warm and busy, with afternoon storms.
Concerts, festivals & local happenings
Check the county visitor site when choosing a weekend, and confirm dates and tickets with the organizer.
06 / Suggested itinerary
Friday in. Sunday home.
A sample Friday–Sunday weekend: the harbor, the ferry and two waterfront dinners. No bookings or availability confirmed.
Day trip version
Just for the day
- Arrive
Land at KESN mid-morning and pick up the car.
- Midday
The Chesapeake Bay Maritime Museum, then crabs at The Crab Claw.
- Afternoon
A stroll around the St. Michaels harbor, then back to the FBO.
FRI
Arrive & Easton
- Late-morning arrival
Land at KESN, subject to weather and your actual flight plan, and pick up the car.
- Afternoon
Check in, then walk downtown Easton.
- Evening
Dinner at Bas Rouge.
SAT
St. Michaels & the water
- Morning
The Chesapeake Bay Maritime Museum.
- Afternoon
Crabs at The Crab Claw, then the spa or a sail.
- Evening
Sunset dinner at Stars.
SUN
Oxford & home
- Morning
Drive or bike to Bellevue, ride the ferry to Oxford and stroll the town.
- Before leaving
Return the car and allow time at the FBO.
- Fly home
Summer storms build over the Bay in the afternoon; let weather set the departure.
Longer stay · Add a day
With an extra day
- Morning
Bikes and the Oxford–Bellevue Ferry to Oxford.
- Afternoon
A sunset sail or a skipjack cruise.
- Evening
Dinner at a waterfront restaurant on Tilghman Island.
07 / Good to know
Keep the weekend easy to change.
These details make the difference between an appealing list and a usable getaway.
Book in this order
Lodging and a car first, then dinners and any spa time.
Airspace
The DC SFRA and military areas are close by. Brief them, and check TFRs before every flight.
Seasons
The ferry and crab houses are seasonal. Check opening dates for spring and late-fall trips.
Dates come next
Rates and restaurant hours are date-dependent. No availability or live price is implied here.
Reviewed · Destination 25
Reviewed November 3, 2026.
Picks and links reviewed by WingAway Weekends. Hours, prices, menus and availability change often, so confirm directly with each place before booking. Spotted something out of date, or have a favorite we missed? Email us at [email protected].
WingAway Weekends helps you discover the destination. Use ForeFlight and current official aviation information for route, performance, weather, NOTAMs and preflight decisions. Flight planning and PIC responsibility stay with the pilot.