My friend and I wanted to do a sort of walk-along with the Hobbit as a sort of exercise project. I guess what I'm asking is how long their journey was, both in terms of miles and months! We want to do it up until Durin's Day, which is my birthday this year!
What a fun project! Well, here’s what I can tell you: Bilbo and the dwarves left Bag End on April 27th, made it to Rivendell by Midsummer, and arrived in Laketown on September 22. So all in all it was about five months.
As for distance… Tolkien never got all that specific with the distances himself, but according to Karen Wynn Fonstad’s Atlas of Middle Earth, the estimated distance between Bag End and Rivendell was a little over 450 miles, and then from Rivendell to the Lonely Mountain it was a little over 550 miles. So in total about 1,000 miles!
If you haven’t already, you should check out The Eowyn Challenge, which has set up walking challenges from Bag End to Rivendell, and then from Rivendell to the Lonely Mountain. They map out how many miles you should be walking a day, where in Middle Earth you’d be at any milestone, things like that - could be a great source for you and your friend. Good luck!