10) Boston Post Road/(Putnam Avenue)
It's a lot of fun to drive down the Boston Post Road on Christmas day. Having been born and raised in Greenwich, I have seen a ton of changes on this street, but one that has always been true is that it has held a lot of traffic, except on Christmas day! It's a lot of fun to drive through town in areas that are normally busy and witness a rare quietness and peacefulness with lights glittering everywhere.
9) & 8 ) Hendrie Avenue & Owenoke Way
Driving right through the heart of Riverside during the holidays is always special. Christmas lights everywhere and kids smiling from ear to ear waiting for Santa.
7) North Street
I have no clue what it costs to light a 90 foot spruce, but it looks fantastic. If you want to see some impressive Christmas decorations take a drive up North Street.
6) Tod's Point/Greenwich Point Park
I don't know what it is about the 150 Acres of Tod's Point/Greenwich Point Park that gets me going, but it has to be one of the best public parks in the country. I'm not one for summer beach time (I can't sit down for more than 5 minutes), so the off-season is actually my favorite time to come. If you drive through the park and stop on the north western side facing all of the waterfront real estate you'll see some pretty impressive decoration.
5) Orchard Street
For those of you who enjoy santa and reindeer, driving through Cos Cob in the winter time will give you some great displays of the big old guy and his horsepower.
4) Sound Beach Avenue
There's something about a retail/town street with its trees and lampposts all lit up.
You've seen me post all about Round Hill Road and the fantastic real estate on this fantastic road. I truly believe it is one of the best driving roads in the north east (behind the Merritt of course). The experience only improves over the holidays (as long as you drive when its dry).
2) Belle Haven/(Harbor Drive)
1) Greenwich Avenue
No matter where I spend Christmas I always seem to think about Greenwich Avenue in the month of December. It's NOT because of the shopping. It's because of the atmosphere.