It’s easy to forget that the yearly trips Michael, Orvis, and I take to Vermont every August started as little more than a late summer work trip in 2012. At the time, we had lived in New England for four years and still hadn’t been to Vermont. Since that first wonderful trip to the Green Mountain State, we’ve been back a number of times, at various points throughout the year, and continue to fall even more in love with the state, but it sure is hard to beat our summer visits to Vermont.

This August’s destination was Woodstock, a town that will always hold a very special place in our hearts, as it is where we traveled right after we were married last fall. The Woodstock Inn, we’re thrilled to report, is still as dog-friendly and inviting as it was back in November, and the town is just as charming, if not more so, in the summer when yards and gardens are at their very best, and the streets and square are bustling with people.

On this trip, wanting to slip into our Vermont vacation mindsets as quickly as possible after we arrived, we grabbed the bottle of champagne we were greeted with in our room, picked up some Plymouth Cheese at the farmer’s market in the town green across the street, and headed up Mt. Tom for an evening picnic on the mountain. The views of town and the surrounding area from the overlook on Mt. Tom are spectacular on almost any day, but having the trail and area at the top almost entirely to ourselves made it all that much more special.

We spent the following day reacquainting ourselves with the town, selecting our favorite homes (mine is pictured in this post). We visited the inn’s beautiful spa together, ate lunch by the pool, and hiked up Mt. Peg for the first time with Orvis.

That night we returned to a special spot for dinner, the restaurant in Ludlow we’d visited on that very first trip to Vermont back in 2012, The Downtown Grocery. With an emphasis on southern cuisine and the freshest local produce, The Downtown Grocery impressed us just as much as it did three years ago.

On our final morning, we took another stroll through the nearby Marsh-Billings Rockefeller National Historical Park before checking out. Although leaving Vermont is definitely the hardest part of every trip to the state, over the years I’ve learned (and am convincing Michael) that the best way to ease the pain of leaving is to stop by Farmhouse Pottery to add another beautiful piece to our slowly growing collection. As we drove back through town we realized we weren’t quite ready to leave, so in an attempt to prolong our vacation just a few hours longer, we stopped for a picnic on the front lawn of the Woodstock Inn, a pleasant way to cap off another perfect August trip to Vermont.

Photos by Meredith Perdue for Map & Menu.