As Tara said, it depends where you are coming from. There are four main ways to get to OC. Coming from Route 50 you need to cross the Route 50 bridgeacross the Sinepuxent Bay into OC. Coming on Route 90 you need to cross the bridges across the St. Martins river and the Assawoman Bay. Coming south down DE Route 1 you will need to cross the Indian River Bridge. None of these are huge tall bridges like the Chesapeake Bay Bridge. The Route 50 and Indian River Bridges are both less than a mile long. The Route 50 and route 90 bridges are probably only about 40 feet off the water. You can take DE Route 54 from Route 113 to Fenwick Island and then take coastal Highway South into OC you will not cross any notable bridges.
If you are not from the eastern shore you have some other challenges dealing with the Chesapeake Bay and theDelware Bay/River. These bridges are much more significant than the ones into OC. If you are coming from the the South (e.g., Norfolk) you need to take the Bay Bridge Tunnel. If you are comming from the West (e.g., Baltimore, Washington) you need to take the Chesapeake Bay Bridge. If you are coming from New Jersey or north you need to cross the Delaware Bay Bridge or one of the bridges into Philadelphia. You could cross the Delaware Bay on the Cape May Lewis Ferry, but then you will still need to cross the Indian River Bridge. The final set of bridges that could be a problem are the ones across the C&D canal. If you come from eastern Pennsylvania or northern Maryland you can avoid all bridges except the C&D bridges by going across the north end of the Chesapeake Bay and then taking 113 to 54 to OC.
Sorry that I could not give a more direct or better answer, but there is really no way to get to OC, other than by boat, without crossing some significant bridges.
Answered: June 1, 2011