When we rolled up into Manchester, Vermont that first time, it was already a bit dark. We made a few wrong turns, but each turn took us back to a main road. With each quiet street we came to the realization that maybe Manchester wasn’t that big. Maybe it was small. Maybe it was the escape from our home in Brooklyn we were looking for. But what would we do for three days we wondered? Well, after the addition of three littles and after ten years of escaping the grit of NYC in Manchester, we’ve finally pegged exactly what to do in Manchester, Vermont when you’ve just got three days to soak it in.

(Side note: there are a ton of places to stay in Manchester, from chain hotels to cute B&Bs. Whatever your preference, you can find accommodation. We always stay at The Equinox Resort and Spa.)

What to Do in Manchester, Vermont: Day 1

Up for Breakfast

Our first stop upon waking is at a small breakfast restaurant in town: Up for Breakfast. There is a small sign hanging from the storefront over a set of wooden stairs leading “up” to the restaurant. Chances are, you’ll be able to find it based upon the crowd of people milling about the bottom of the stairs, anxiously awaiting their names to be called.

The second-floor restaurant itself is tiny. I mean itty bitty. The tables are jam-packed with people and the smells of the food overtake you when you walk in. After we stop and put our name in, learn what our wait time will be, we grab a cup of coffee and settle in, whether it’s ten minutes or fifty.

What makes us willing to wait this long with three hangry little ones? It’s not the service. They move quick and are no frills, which at first made us think that they were angry with us, but after ten years of being served by the same people on each trip, we know it’s just an efficiency that has to happen when you’re moving this many hungry people through one tiny space.

If it’s not the people, then the only thing left is the food. And I can’t say enough for the food. I spend nearly every morning of the rest of my year, thinking about this breakfast. The corn bread, the pancakes, the sausage, the bacon, the toast, the coffee, the flavored coffee (which changes), the turkey hash. I could go on. The menu is endless and filled with a number of unexpected goodies, not to mention specials.

Bookstore

The next stop on day one is the Northshire Bookstore, which is a five minute walk from Up for Breakfast along the Main Street. Before entering, be prepared with some ideas of what you want or an entirely open day because this book store is nooks and crannies filled with books of all topics. And that’s just the bottom floor. Ask anyone around what to do in Manchester, Vermont, and this little (or rather big) bookstore comes out of their mouths first.

Head up the giant iron staircase and it is a little person’s heaven. We usually head directly here. My little ones wander around and we let them all pick a book or two. Then, for the younger ones, it’s to the front of the building (still on the second floor) to play with train tables, puzzles, and all the other odds and ends that are in the little room. And for the older one, she heads to the back of the building (still on the second floor) and crawls up the ladder into a little reading nook to sort out all the books she’s deciding between.

Shopping

After we let our food settle in the bookstore, we make our way back to our car. From here we head out to get in some shopping at the Manchester Designer Outlets. This includes a number of stores spread throughout town rather than an entire shopping center. You can find shoes, clothes, home goods, bags, and any number of items. For us it means just a stop or two to fill in our little ones’ ever changing winter wardrobes. But the shops here are uncrowded and manageable, even for those who don’t manage shopping well (and I’m not just talking kids here).

Lunch

By now it’s late in the day, well past lunchtime, but that doesn’t mean those amongst us who can’t tell time yet don’t want some reliable lunch (no matter how close dinner may be). We swing by The Works Bakery Cafe for some sandwiches and a pick me up before meandering our way back to our hotel to sit on the back porch and fill our bellies.

Hike to Lake at Equinox Preserve

After recharging, we head to the Equinox Preserve. Though we can get there from the hotel we stay at, we still drive our car to the uppermost parking lot, saving our little ones a great deal of an uphill climb. Then, it is a short walk from the car to the trail that runs horizontally along the mountain, so perfectly flat for little legs that struggle to keep up (aside from the rocks dotting the scenery that make for perfect perches to jump from).

At the end of the trail, around a small curve, is the entrance to the Lake with the mountain towering behind it, like a postcard. It’s small, it’s peaceful (until my littles get there at least), and it’s beautiful. We sit and soak it up. We throw rocks and give lessons on rock-skipping that result, merely, in rock-kerplunking. Then we set out, a little weary, for the short, flat hike back to the car.

Dinner

After years of trying places near and far, we’ve come to the conclusion that the food is good in so many places, so we opt to choose out of convenience. After we bath our little ones, we usually set out, purposely avoiding our car, knowing that after a day of food, shopping, and hiking, the car’s rhythmic motions will put them to sleep–before dinner (and ain’t no momma trying to deal with eating dinner with a sweaty sleeping toddler on her lap).

Our first night, we usually just pack up the littles and walk down the road to The Coppered Grouse. Here, they’ve seen our little ones on their best days and they’ve seen them on their worst days, and on those worst days, they’ve been gracious enough to grab that extra glass of wine a little bit faster.

Note: There really is no shortage of great places to eat in Manchester, but what’s key is making sure to get a reservation or run the risk of eating much later than little people can handle.

Calming Down and Wrapping Up

This day usually runs so late, that the littles are ready to fall asleep by the time we get back to the room. We tuck them in (some sleeping in teepees), and barely have a moment to slip into some warm clothes before they’re fast asleep.

Because we’ve scouted out this hotel and been staying in it for years, we always stay in the same room because of its proximity to the back deck. Here, we turn on our monitors, head to the back deck, and relax under the Vermont sky.

What do Do in Manchester, Vermont: Day 2

Little Rooster Cafe

Day two gets a little contentious in the morning. Because some of us do not like change. (Me. It’s me who doesn’t like it.) And to tell the truth, we have, historically, gone every morning to the same place, Up for Breakfast. But the last two years, we’ve gotten a bit adventurous and spread our wings. Part of the reason is that it always seems that every breakfast place in town is surrounded by buckets and buckets of people patiently standing outside waiting for a table every morning, all morning long. And being nosy, we kind of want to know why.

On our first real adventure breakfast (that’s what we’re calling them now) we went to Little Rooster Cafe. It was cute and had a sweet little ambiance. And the food was quality breakfast food. We certainly didn’t leave disappointed in our decision to venture out, which is good because we needed fuel for our next adventure.

Stratton Mountain

After a nearly half hour drive, we pull into a parking lot of Stratton Mountain, which, though it’s not ski season, has plenty to offer my little people in the off season, starting with a stroll through the pedestrian only village, lined with little shops and restaurants and filled with families and friendly dogs on leash.

At the end of the village we head to the Stratton gondola and get in, watching the world shrink as we slide higher and higher into the Green Mountains (the bonus is children four and under are free). At the top of the mountain we take a small hike, usually the Beginner Fire Tower Trail. Though it makes little difference to my people, it invigorates me to know that I am walking to the spot that inspired both the Appalachian and the Long Trails.

After checking out the view of four states from the Fire Tower, my tuckered little people, who have also repeatedly stopped to pick wildflowers along the way, happily crawl back into the gondola and relax for the gentle ride back down to the mountain.

Here we meander back through the village. We find a band to watch and local animal wildlife rescue that teaches our little people about owls and snakes and all sorts of creatures. Then, finally we pick one of the number of restaurants to relax and have a late, well-deserved lunch at. It’s super important to fill those bellies because after a good hike, fresh air, and a full belly, a half hour car ride should be enough to set them adrift in a world of unicorns and fairy tales.

Swim

After a day filled with so much clean air and open spaces, my littles (and those grown ups who take care of them) crave a bit of down time, so we always hit the pool before a bath and dinner. We’re fortunate that the hotel we stay at has an indoor pool, so regardless of the weather, we take advantage of this amenity. But even if a pool isn’t an option, spending some down time close to “home” is enough. The Vermont sky at dusk is a wonder to sit back and watch. Back porches on lounge chairs, front porches on rocking chairs, sidewalks with bikes: regardless of what it is, we always keep this night of adventure a little less adventure-filled.

Dinner and Bed

The second night, it’s back out to dinner in one of our favorite, walkable, spots because there’s no denying that a short car ride would bring on a nap that would result in a child waking in the middle of the night wide-eyed and hungry. And that’s just not something any of us want to deal with, especially if we have to be sharing rooms. (Need tips on exactly how to share a room with your infant or toddler? Check out our “Tips for Sharing a Hotel Room with Your Infant or Toddler.”)

After dinner, we put on a few layers of clothes (some nights in Vermont can get a little chilly) and we head out to the fire pit at our hotel, sipping some wine while our kids play in the grassy courtyard until it’s time to head up to our room for tuck ins, which happen fast thanks to the day’s activities.

What to Do in Manchester, Vermont: Day 3

Breakfast

This is pretty standard now. We always head back to our favorite spot to order one more Hungry Hiker or one more Turkey Hash before our trip is done. We wait however long we must; some things will just always be worth it. (The real reason we always used to end up here is that I was a vegetarian a long, long, long time ago. This lovely little place was not only one of the only places I knew that served vegetarian bacon, they were the only place I knew that made it well. Like really really good.)

Drive to top of Mt Equinox (Skyline Drive)

Not far from Manchester proper, along 7A in Sunderland, is the Toll House entrance to Skyline Drive, the longest, privately-owned paved toll road in the United States at 5.2 miles long. It meanders (really it switchbacks) up 3,248 vertical feet, providing some great views and some white-knuckle moments (at least for the Three Kids’s Dad) as you drive along the crest of the mountain to reach the summit 3,848 feet above sea level, which is the highest peak in the Taconic Mountain Range.

Once at the summit, there is the Saint Bruno Viewing Center, which has a place to rest, picnic areas, viewing platforms, and rest rooms. The building also houses a vast amount of information on the mountain and the Carthusian Monastery, which can be seen along the road that runs the crest of the mountain. Additionally, there are a number of hiking trails leading from here, including one that leads to Look Out Rock. It’s a short, easy trail ideal for kids. From lookout rock a view down into Manchester can be seen.

Ice Cream

After having made our way back down from the summit, we head back towards Manchester on 7A. Along this route, on the left, we stop at a small turn that looks as though we’re headed into the driveway of a farm. And we are. But this farm makes ice cream. Wilcox Ice Cream is as delicious as any homemade ice cream can be. Drive up the dirt road to the red shack and place an order. We then relax on the picnic tables, surrounded by the sound of cows mooing in the distance and wind rustling through the tall grasses. And this. This giant vat of ice cream? We call it lunch too.

Feed fish at Orvis

After our creamy feast, we head back into town and stop at the Orvis Fly Fishing School and Store. Once here, we pile out of the car and spend a little time feeding the fish that are leisurely swimming around in the pond. They gobble up all the little pellets we have, and here we just stay for a while, watching them move effortlessly, and rest from the day’s adventures.

Dinner and Night, as Usual

We close our Manchester visit out by heading back out to one of those restaurants we adore. This night, we might risk it and head out in the car, but our car ride still takes us less than five minutes. The day was eventful, but not exhausting, as the summit hike was less than a quarter of a mile and most activities we got to by car rather than on foot. This is the type of day we leave for the last, as two days of fresh air and hiking have made for fairly tired little people (and grown ups who have often carried those tired little feet).

Manchester can be a dream destination, no matter the time of year. Our littles are, by no means, wonderful hikers. We usually have some tears and some whining, but there are so many trails in the area, that it’s easy to find ones manageable for them all. And because there are so many simple ways of reaching the summits of surrounding peaks, those hikes don’t have to be “boring” hikes either. They can have views, and traveling to the top can be an event in and of itself. Vermont is more than the mountains though. It’s slowing down. It’s good food. It’s fresh air. It’s family.

Those are the reasons we keep coming back to Manchester and never seem to be bored. And sure, our “What to Do in Manchester, Vermont” list changes from year to year because we know we’re going to be coming back and there are a million ways for us to spend our time. But this is an itinerary of our absolute favorite ways to pass our days together, deep in the beauty of the Vermont mountains.

Do you have any towns you keep going back to? Even to do the same things again and again? If so, I’d love to hear about them and maybe get a chance to check them out. Tell me about them in the comments!

Happy Travels!