Dolly, Penny and ??
 

Anyone know what the names of the other two islands are next to Dolly and Penny? They're too small on my maps.

Is there a story about Penny? Dolly was named after Dolly (Bryant) Nichols who was quite a character according to what I could find out about her. She operated a ferry ("rowboat") and also ran rum from the Weirs to sell to the fishermen.

'Hope This Helps...
 

Not my area of particular interest, but thought I'd pass along a "note" from a 1994 chart:

Bizer says...
 

According to Bizer, there are 5 islands there (in table form):

size, name, notes
5, Dolly, Just off Bear I, 420m NE FL#3; 1080m WNW FL#29
4, South Dolly, Just E Dolly I. (see notes)
4, Little Dolly, just S South Dolly. South Dolly & Little Dolly have a small channel cutting it into two islands.
2, Penny, Large rock just NE South Dolly; 500m NE FL#03 (Formerly thought to be Piano Island)
1, Piano, Large rock 25m E Little Dolly; 25m SE South Dolly

U.S. Geological Survey maps of Lake Winnipesaukee show an island named "Penny" about 75m SE of Dolly Island about 400m NE of light #3. This island is really two islands which are cut in half by a narrow channel not shown on Bizer's chart. From 1996 to 2013, these were called Penny#1 and Penny#2. Bizer has been told these two islands are named South Dolly and Little Dolly. The island thought to be Piano Island is now Penny Island. A previously-unknown island, 25m east of Little Dolly Island is the real Piano Island.

http://bizer.com/winislan.htm

Thanks for the info ApS and Bear Guy. I appreciate you getting back to me on this. I kayak through there and often wondered what the names are. There's a neat little cove between South Dolly and Piano. Fortunately the water is shallow otherwise people would probably anchor in there.

Supposedly, according to local lore or something, the picturesque cottage and boat house on Dolly Island were built in the 1930's by inmates from a prison. It's a super duper spot that gets the setting sun.

It is a great spot but the boat traffic is crazy. They really need to create a no wake zone there.