Updated: Oct 29, 2020

You really can’t get more “fall” than Vermont in October. My BFF and I went last fall and it was a ~*dream*~. If you’re comfortable traveling right now, we’d highly recommend putting VT at the top of your trip list. (See travel information for Vermont re COVID here). If not, save this inspo for next year when we’ll all hopefully be able to travel again, without fear or restrictions.

While we would have loved to spend more time here, we only had three days. So here are our top picks for your long weekend in the Green Mountain State.


No trip to Vermont would be complete without checking out this small lakeside city. The waterfront is gorgeous, Church Street will have you wishing you lived here, and the vibe is indescribable. From college students to families, everyone you come across is friendly and spirited. Vermonters are also super active and passionate about the environment (although with all of the world-renowned skiing, hiking, and boating here

, who wouldn’t be?!), so the recreation options are endless.

American Flatbread: Hands down, one of my most favorite restaurants. Pizza so good you can’t even feel guilty about it - American Flatbread focuses on high-quality ingredients; they call it “pizza with integrity.” They are also home to Zero Gravity Brewing. If you’re here on a weekend, be prepared to wait (unless you’re able to make a reservation). If the small bar is crowded, there are a few other options within a minute walk to grab a drink while you wait for your table: try Drink or Vermont Pub & Brewery. (It’s so worth the wait). We ended up only having to wait about 15 minutes before we were seated in a cozy booth and presented with an impressive drink list. The oven is open into the dining room so you can see the delicious pizzas being prepared and fired. I’ve been here a few times and every single pizza I’ve tried is amazing, but my favorites are the New Vermont Sausage and Medicine Wheel. Check out their website here.

Church Street Marketplace: Local shops, chain stores, farm to table restaurants, breweries, bars, and live performers all along a brick-paved road closed to vehicles for your pedestrian pleasure. Grab a treat from Lake Champlain Chocolates as you window shop and take in the music. We happened to be here during a parade and farmers/craft market. Check out the shopping, dining, and event guide here.

Foam Brewers: The best patio of our trip. No matter what time of year you go, dress for the weather so you can enjoy your brew outside looking out to Lake Champlain and the Adirondack Mountains on the other side. They have a great selection of beers with some unique offerings. If you’re hungry, they also have light snacks, apps, and sandwiches. It’s worth noting that even “bar fare” at a place like this in Vermont is probably better than a lot of “restaurant fare” wherever you’re from. Also worth noting: This is one of the only places in downtown Burlington with ample free parking. Check ‘em out.

Citizen Cider: If you live in the northeast, you may have enjoyed their cider before. Check out their Pine Street location to enjoy a flight or craft cocktail, buy cans of their cider or other merchandise, order food, and grab a table on the patio.

Try a maple cremee: “A what?!” you ask. Maple flavored soft serve ice cream. It’s a local favorite and something everyone should try. You’ll see stands and signs all around town, so stop and get one!

Mount Philo: If you like easy-moderate hikes with incredible views (you gotta work for that cremee!), this is the place for you. Visit the State Park's website for more info.

Other honorable mentions: Switchback Brewery, Beverage Warehouse in Winooski (lovingly referred to as ‘The Bevvie’ by locals) to stock up on Heady Topper and your other favorite VT beers (they sell wine and liquor, too), Sneakers Bistro in Winooski for brunch, ride the ferry, ECHO Leahy Center for Lake Champlain, have a drink on the rooftop at Hotel Vermont

Stop at Ben & Jerry's in Waterbury: You kind of have to do this. The most famous ice cream company in the country (the world?) is based here and they have a huge warehouse for you to tour - complete with a free sample. You can spend a couple hours here enjoying the photo ops, gift shop, Flavor Graveyard, and of course getting a scoop or two of your favorite stuff at their scoop shop on-site. The tour is very informative about the two guys who started it all and their commitment to sustainability, democracy, and social justice. Read all about the factory tour here. Tour: $4 for adults, $2 for kids (due to COVID, tours are temporarily suspended)


The most Instagram-worthy town you’ll ever go to. As soon as we drove in, I immediately fell in love and couldn’t wait to park the car so we could walk around and take it all in. I hope I don’t do a disservice to the town of Woodstock by saying it reminds me of a Hallmark movie. "Quintessential" and "charming" are words you will likely come across while researching this town. Quaint, historic, and beautiful, it’s the perfect spot for a romantic getaway and I couldn’t help but think about coming back here with my fiancé.

Stay at an inn: With a lot of options to choose from, it can be hard to decide. The most iconic and well known, The Woodstock Inn (rates vary drastically by date & season), is located in The Green and features multiple dining options, pools, a golf course, and much more. Other top-rated options include The Charleston House, Jackson House Inn, and The Blue Horse Inn.

Wander about town: Take in all of the beautiful old homes and inns around the Green. Chartered in 1761, most homes are of the Georgian, Federalist, and Greek Revival style. The unique, and some eclectic, small shops are perfect for looking for gifts (including for yourself!). We especially enjoyed The Vermont Flannel Co and Red Wagon Toy Co.

Check out the covered bridges: Covered bridges aren't unique to Vermont, but if you're not from the northeast, or if you live in a more modern, developed area, you probably won't come across them too often. The roofs and sides protect the wooden bridge from harsh weather and snowfall. You can check out four covered bridges while in Woodstock, one of them right in the center of town - Middle Bridge.

Mon Vert Cafe: Great breakfast, lunch, and coffee in a nice atmosphere. Like so many other eateries in Vermont, they boast using organic, local ingredients. It's a great place to grab a coffee and sandwich or bagel on your way out of town.

Long Trail Brewery: The. Nicest. Staff. We had an amazing experience here, even though we rolled in an hour before closing on a Sunday. All of the staff greeted us warmly and even gave us additional samples for our beer flights, told us about the brewery and area, and helped us pick out some specialty beers unavailable in NY to bring home. They have a good size indoor space with a bar, gift shop, and seating area, as well as an outdoor patio.

Worthy Kitchen: While we didn't have a great service experience, the food was very good and we've heard great things from others, so we'll chalk it up to a bad night. If gourmet mac and cheese, burgers, and BBQ pork sound like your jam, give it a try.

If time allows: Quechee Gorge, Simon Pearce, Cloudland Farm, Billings Farm and Museum

If you have an extra day or two, check out Stowe!

Please do your research before planning a trip, as the rapidly evolving and changing COVID-19 situation will likely affect businesses' hours of operation and reservation policies.

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