A Guide to the Best Events in Maryland 2026 and How to Get There in Style
What is worth flying in for? A season-by-season itinerary of Maryland's 2026 events, each paired with a place to stay and the vehicle we would send.
Visitors ask our chauffeurs the same question in different accents: what is worth flying in for? Maryland's 2026 calendar has a real answer for every season. This itinerary-style guide pairs each event with a place to stay and the vehicle MSY Limo Service's Maryland fleet would send, so you can plan the weekend from wherever you are reading this.
Spring: Racing Silks and Dress Whites
Preakness Stakes, May
The 2026 Preakness ran at Laurel Park while Pimlico is rebuilt, and the race returns to Pimlico in 2027. Laurel Park sits minutes from our base, so stay at a BWI-area or Columbia hotel and book a Cadillac Escalade for six or a Sprinter for a hospitality-tent group. Details on our Preakness transportation page.
Commissioning Week, Annapolis, late May
Naval Academy families fill every room in Annapolis. Reserve a Main Street or Eastport hotel early and let a chauffeur handle the Academy gate logistics; see BWI to Annapolis car service.
Summer: Harbor Nights and Ocean Air
Artscape brings free art and music to Baltimore each summer, and the Orioles play at Camden Yards from April into September. An Inner Harbor hotel puts both within a short ride; a Mercedes-Benz E-Class sedan suits a couple, and we cover the Camden Yards run daily. In June the Ocean City Air Show roars over the boardwalk, and a Chevrolet Suburban makes the BWI to Ocean City transfer comfortable with beach luggage.
Fall: Maryland's Busiest Season
Maryland State Fair, late August to early September
Stay in Towson or Timonium and ride a Suburban to the fairgrounds; our State Fair transportation page covers pickup points.
Maryland Renaissance Festival, late August through October
Crownsville's festival weekends pair well with an Annapolis hotel. A Sprinter van keeps a costumed group together on one flat rate; see Renaissance Festival transportation.
Annapolis Boat Shows and Sunfest
The Sailboat and Powerboat Shows take over City Dock in October, and Sunfest closes Ocean City's season in September. For the boat shows, book an Annapolis hotel far in advance and a BMW 7 Series for client entertaining; our Boat Show transportation page has more.
Navy football and Ravens Sundays
Navy-Marine Corps Memorial Stadium hosts fall Saturdays and M&T Bank Stadium hosts the Ravens from September to January. Group tailgates ride best in a Sprinter; see Navy stadium transportation.
Winter: Lights on the Harbor
Christmas Village at the Inner Harbor runs November into December, and Hampden's Miracle on 34th Street lights glow through the month. A stretch limousine tour of both is a favorite for visiting families staying downtown, and the Ravens keep M&T Bank Stadium busy into January.
Getting There in Style
Every event above is served on flat rates with no surge, flight tracking on airport legs and 24/7 dispatch. Popular weekends sell out weeks ahead, especially Sprinters and limousines, so reserve online or call (877) 609-1919 once your hotel is booked. Our special events page explains hourly options for a full day out.
Frequently Asked Questions
Was the 2026 Preakness at Pimlico?
No. The 2026 running was held at Laurel Park while Pimlico Race Course is rebuilt; the race is scheduled to return to Pimlico in 2027. We serve both tracks from our Laurel base.
Which vehicle is best for a group going to a Maryland festival?
A Mercedes Sprinter for up to 13 keeps everyone together on one flat rate. Couples usually prefer an E-Class sedan; families with gear choose a Suburban or Escalade.
How early should visitors book event transportation?
Two to four weeks for most weekends and six or more for Preakness, Commissioning Week and the Annapolis Boat Shows. Call (877) 609-1919 as soon as your hotel is confirmed.
Can you combine an airport pickup with an event transfer?
Yes. One reservation can cover the BWI, Dulles or Reagan arrival, the event run and the return flight, with flight tracking and 45 to 60 minutes of complimentary wait time on arrivals.
Can you provide child car seats?
Yes. Infant, convertible and booster seats are available on request — tell us the child's age when you book and the seat is installed before the vehicle arrives.
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