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Scott,
Hudson Creek in the Little Choptank would be a well-protected anchorage that time of year. It's a nice little anchorage, quiet and isolated. I second the other suggestions about stopping in Crisfield. We always ate dinner at Fisherman's Inn there. You can anchor in the Somers Cove Marina basin, off the Coast Guard Station, but the bottom is soupy mud. You might drag if the wind kicks up to 30 kts or more.
From Crisfield, I'd suggest heading south to Onancock, at the head of Onancock Creek, about five miles off the Bay on the eastern shore of Virginia. Some good restaurants there, too. There's room to anchor, or you can tie up to the bulkhead at the little Onancock Wharf marina. It's less than 30 nm from Onancock to Deltaville. If you're not ready to end your trip, try Mill Creek, off the Great Wicomico River, south of Smith Point on the western shore in Virginia. It's very well protected from all wind directions, and fairly unpopulated by houses on the shoreline.
Hudson Creek in the Little Choptank would be a well-protected anchorage that time of year. It's a nice little anchorage, quiet and isolated. I second the other suggestions about stopping in Crisfield. We always ate dinner at Fisherman's Inn there. You can anchor in the Somers Cove Marina basin, off the Coast Guard Station, but the bottom is soupy mud. You might drag if the wind kicks up to 30 kts or more.
From Crisfield, I'd suggest heading south to Onancock, at the head of Onancock Creek, about five miles off the Bay on the eastern shore of Virginia. Some good restaurants there, too. There's room to anchor, or you can tie up to the bulkhead at the little Onancock Wharf marina. It's less than 30 nm from Onancock to Deltaville. If you're not ready to end your trip, try Mill Creek, off the Great Wicomico River, south of Smith Point on the western shore in Virginia. It's very well protected from all wind directions, and fairly unpopulated by houses on the shoreline.