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Hartford to Ludlow to Boston

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My husband and I are going to a family reunion in Ludlow Vermont at the end of July and have several legs of this trip and need suggestions for all of them, so here goes:

Part 1 (Hartford CT to Ludlow VT): We are flying into Bradley International Airport on Saturday (arrive at 4:00) and are planning on getting a rental car at the airport and driving up into Vermont somewhere to stay the night on Saturday night (check in at the reunion is on Sunday morning). We were trying to find something off of Hwy 91 or 103 so that we don't go too far off of the main path. We would Priceline (or something) a hotel for the night and would wake up to drive into Ludlow for the reunion (be there around noon). Any suggestions for a nice town to stay in where we can have a nice (but inexpensive) dinner and a leisurely breakfast before heading up to Ludlow?

Part 2 (Hartford CT): The reunion ends on Thursday morning, so we are going to leave Ludlow and drive back to Hartford with the rental car to do some exploring in Hartford. Again we will Priceline a hotel but are looking for interesting places to go/food to eat/sights to see. We are going to stay Thursday night in Hartford and take a Greyhound bus to Boston the next late morning/afternoon. Since we have to return the car to the airport we found a bus that goes from the airport straight down into the Greyhound/Amtrack station in Hartford, so we were giong to take the bus to the station then take the bus. Any hints/suggestions about transportation that we haven't thought of? Anything interesting to do in Hartford? We're going to go to the Mark Twain House and maybe the Elizabeth Park rose gardens, but again, looking for food/activity suggestions.

Part 3 (Boston MA): We will get to Boston between noon and 3ish and check into a hotel (again, Pricelined). Any suggestions on areas to stay? We will be taking public transportation around and walking, as I hear that Boston is a very walkable city. We would love to do all the touristy stuff, the Freedom Trail, and everything else there. Again, any suggestions for the food/other activities? We will be staying Friday and Saturday night and flying home around 2:00.

Things to know about us: Mid 20's, beer and wine fans, I'm a vegetarian, my husband will eat anything. We like art, history, movies, culture, local things that aren't so touristy (even though we love touristy things too), bookstores, coffee shops, farms, cheese, organic and local eating/drinking, and such. We are on a pretty tight budget so things that are low cost/free are even better. Any and all suggestions welcome! Thanks everyone!

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