Short hand:
1) Ocean Shitty. Condos towering over the beach. Lots of restaurants, boardwalk options and activities nearby incl. go-karts etc. North Ocean City there is a nice park up near the Fenwick border. Predatory towing. Closer to national seashore at Assateague. Seacrets! Fishing harbor.
2) Dewey Beach. Famous as a college kid hang out, can get loud near the Bottle and Cork. Note large state park with an inlet at south end. The area north of Bethany is very quiet.
3) Bethany. "Bethesda on the Beach." Sea Colony has swim lessons for kids on weekday, there are some good restaurants, easy access to decent grocery stores, tennis community, kind of boring and bland but family friendly. New oceanfront homes for rich people. South part of town there are some more affordable homes on the other side of the ocean highway. Parking can be a pain without a pass.
4) Rehoboth. Old money & nice Victorians in north part of town (check out the area around Park Ave.) Small playground at Lake Gerard. Known for being gay friendly but not crazy except possibly at the Purple Parrot, the Frog Pond. Doghead Brewery. Good restaurants, some cute boutiques. The kids will like Funland, an old timey family-owned amusement park geared towards younger kids. Notorious for lack of good parking.
5) Lewes, Del. Northernmost DEL/MD beach. Small, old town with a handful of good restaurants, clustered along a canal/Delaware Bay harbor, Dutch history, main beach is at state park, cute old homes, bay beach appeals to families worried about high surf. Boat rides & fishing. Ferry to Cape May. Low-bridge canal goes all the way to Rehoboth.
6) Chincoteague, Va. Keep going down south on Route 13. Quaint island town, famous for wild ponies. Many modest homes, Wallops Flight Facility w/NASA workers, mobile homes, RV camping, fishing, "Misty of Chincoteague," B&Bs. Drive over a bridge to beach access at national seashore protecting the south end of Assateague Island. Naturey. Lighthouse. No boardwalk or roller coasters excepting rednecky Frontier Village campground waterpark nearby, small arcade/bouncy/bumpercar place in town, mini-golf, pony rides at Pony Centre. Nice playground and fishing dock at Memorial Park (east end of town). Ice cream, fresh seafood, sidewalks roll up by 9:30 excepting Captain Fish's (live music venue.) Gary Howard's for crabs, takeout seafood to cook at home. Mosquitoes problematic.
The rest of Virginia coast down to over-the-Chesapeake-Bridge Virginia Beach are protected barrier islands owned by the Nature Conservancy and difficult to visit. Cedar Island is private and houses are sometime available to rent, access by boat only, from Wachapreague, bring your own groceries. Fishing charters and small motor boats are available to rent in Wachapreague. Some cute towns on the back bay side include Cape Charles, Onancock, Crisfield is crab capital of the earth.
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