Hi Heather,
Ocean City in October can be very romantic. Bed and breakfasts in OC are few and far between. But there are two that I can reccommend.
An Inn on the Ocean is on 10th St and the Boardwalk. It is a lovely place that has been in OC for many years, and is the only B&B that is oceanfront. I have never heard anything but good things about it. And in October, they are having a murder mystery weekend October 22, 23. Their website is
www.innontheocean.com .
The other one I suggest is not on the ocean, but very nice. The Atlantic House is on North Baltimore Avenue, one block back from the boardwalk. They do have some rooms with boardwalk views though.  Their website is
www.atlantichouse.com A good time to visit OC would be the weekend of October 1st and 2nd for Winefest weekend. It is held at the inlet just off the boardwalk. Wine tasting, crafts, vendors, music, and cheeses. There is an admission charge and their website is
www.winefest.com. Also that weekend is the Waterfront Heritage Festival at Sunset Ave. There will be cooking demonstrations, fish cleaning techniques, live entertainment and no admission.
www.ocharborday.com The following weekend (Oct. 7,8) is very exciting with Endless Summer Cruise In. If you're into cars, this is a great weekend to visit OC. Thousands of hot rods, muscle cars, and show cars line the streets and show off their style and parade on the boardwalk. I've attended this event in the past and it is a lot of fun.
www.endlesssummercruisin.com This is also Octoberfest that weekend at 40th St. and the bay at the Convention Center. Lots of crafts, food, and drinks!Â
If you can't make it till the weekend of the 15th, that's Freestate Corvette Club weekend where thousands of Corvettes decend on OC with a big show at the inlet and a parade up the boardwalk. There are usually more than 500 Corvettes that participate in the parade from every generation.
While you're in OC, be sure to take a long walk up and down the boardwalk. Many of the shops will be open and a lot of good restaurants. Try Harrison's Harbor Watch at the very beginning of the boardwalk at the Inlet. Ask for a window seat for the best views of the inlet to watch the boats coming and going. You can see Assateague from there too so you might get lucky and catch sight of a couple of ponies. In the evening, drive up Coastal Highway to 125th St to Northside Park. It is behind the Blue Ox on the left, bayside. You can park your car and take a very romantic walk around the grounds and out to the end of the pier to watch the sunset. Or take a drive to historic Berlin to see the Victorian architecture and shop their wonderful quaint shops.
I hope you have a great time in OC.