With its history, cobbled streets, manicured parks, and countless restaurants, cafes, and shops, Boston has everything I could ever need. And yet each season, I find myself longing to spend a quiet weekend escape in Vermont. Today I’m spotlighting 3 of my favorite cities in Vermont: Brattleboro, Woodstock, and Burlington (ranked from closest to Boston to farthest from Boston), and my best tips on what to do, where to eat, and where to stay.
Hours from Boston: 2h 15min (daytrip-able, in my opinion)
Things to do in brattleboro:
Hiking Wantastiquet Mountain // Though technically in New Hampshire, this approachable 3.9-mile trail is less than one mile from Brattleboro, just on the other side of the Connecticut River. The views at the summit are impressive, especially when the fall foliage is popping. If you’re looking for a more intense hike, Mount Monadnock is about an hour East of Brattleboro.
Apple picking at Green Mountain Orchards // There are plenty of places to go apple picking much closer to Boston, but this one is worth the drive, as it never seems overly crowded. They also have pick-your-own pumpkins and warm apple cider donuts, in addition to a farmstore with other local specialties. The orchard is only a 20-minute drive from downtown Brattleboro.
Hidden Springs Maple // This cute little maple syrup store is less than one mile from the apple orchard. Since you drive past it on the way to the orchard anyway, it’s a no-brainer to take a quick pit stop inside and stock up on real Vermont maple syrup.
Downtown Brattleboro // Brattleboro is like a smaller version of Burlington, VT. There are lots of cute shops, restaurants, cafes, and bookstores. While you wouldn’t need to spend a whole day there, it’s a cute place to walk around while you’re waiting for a table (see below).
Where to Eat in Brattleboro:
Whetstone Station Restaurant and Brewery // It is so difficult to visit Brattleboro and not eat at this restaurant (red building in the photo above). The beer selection is fabulous, and in addition to your typical bar food (burgers, etc.) I have always been pleased to find veggie-centric dishes as well, such as a quinoa bowl with local vegetables. There is always a wait for a table, especially on pleasant days when the roof deck is open (the restaurant overlooks the Connecticut River), so it’s best to put your name on the wait list before you get hungry, then stroll around downtown Brattleboro until your table’s ready.
Duo // On my most recent trip to Brattleboro, the wait at Whetsone Station Restaurant was too long to bear, and we needed to get back on the road at a reasonable time. So we wandered along Main St. until we stumbled on Duo, a super charming, Insta-worthy, farm-to-table restaurant that serves dinner and weekend brunch. Though they don’t offer a lunch menu, we managed to snag a seat while brunch was still being served. The food was delicious (I got a grilled cheese sandwich on multigrain bread with gazpacho) and the atmosphere was lovely!
Mocha Joe’s // For fans of unsweetened chai lattes, the chai at Mocha Joe’s is hard to beat!
sample itinerary for brattleboro:
Hours from Boston: 2h 30min
Things to do in Woodstock, vt:
Skiing at Killington, Pico, or Okemo // Nearly every visit to Woodstock has revolved around a ski trip. Killington & Pico are about 30 minutes West, while Okemo is about 35 minutes South.
Pottery Workshop at Farmhouse Pottery // I’ve long admired the beautiful dishes and accessories from Farmhouse Pottery, and when I found out that they also offer workshops, I checked out their website immediately. At $350 per couple (for a tour, personal pottery lesson, & wine/cheese), I haven’t quite been able to convince my date to split the hefty cost with me. But this this is definitely on my Woodstock wishlist!
Downtown Woodstock // Downtown Woodstock is pretty small, with just a few shops and cafes. But the town also home to charming New England houses and a picturesque covered bridge.
Where to Eat in Woodstock, VT
Simon Pearce // This luxury glassware and pottery mill is home to a beautiful restaurant and bar in Quechee, VT (less than 20 minutes from Woodstock) that overlooks a waterfall and covered bridge. Travel & Leisure magazine named it as one of the most romantic restaurants in America, and the designation is well-deserved. In addition to a stunning interior, the restaurant also serves up delicious, upscale farm-to-table fare.
Long Trail Brewery // If you want to enjoy a flight of local beers with your lunch, Long Trail is a fun place to hang out. Plus, it’s only a 10-minute drive from Woodstock.
Woodstock Farmers Market // This specialty food store and deli has an impressive selection of sandwiches, bakery items, and more. It’s a great place to pick up a quick lunch for a picnic.
Where to Stay in Woodstock, VT
506 on the River Inn // This hotel is honestly the reason I go to Woodstock so often. Ranked one of the best new hotels when it opened a few years ago by Conde Nast Traveler, this beautiful boutique hotel looks like a Restoration Hardware catalog come to life. An impressive breakfast is included, which helps you swallow the hefty price tag (about $300+/night during weekends in the peak season). There’s also a well-kept indoor pool and hot-tub, and a gameroom with boardgames and a pool table. (Families will appreciate the kids play rooms as well). We were cooped up here during a polar vortex once, and were SO thankful that we sprung for a comfortable hotel (think heated towel bars in the marble-clad bathroom) with things to do and a cozy fireplace to read by. If we don’t want to drive much further after a long day of skiing, we book a reservation in the hotel restaurant, or snag some seats at the bar. The menu is surprisingly nice and I’ll take any excuse to spend some extra time in front of the crackling fire.
Woodstock Inn // This classic hotel is a landmark of the area. During peak seasons there’s often a 2-3 night minimum, which is why I’ve yet to have an opportunity to check it out for myself. The gorgeous inn is also home to a spa, a golf course, and restaurants. A must on any Vermont bucket list!
Hours from Boston: 3h 30m
What to do in Burlington, VT
Hiking at Stowe Pinnacle Trail // About a 45 minute drive from Burlington, this trail is 3 miles out-and-back, and is rated as “moderate.”
Skiing // Burlington is about an hour from Smuggler’s Notch, and about 1h 30 min from Jay Peak.
Biking the Island Line Trail // If you’re a fan of biking the Cape Cod Rail trail, then the Island Line Trail is a must if you visit up north. The trail is 13.4 miles each way, and follows part of what used to be the old Rutland Railroad track. Along the way you’ll be treated to beautiful views of Lake Champlain interspersed with lush greenery.
Kayaking, Paddle boarding, or Sailing in Lake Champlain // Just a 10 minute walk from Church St, the main drag of Burlington, and you’ll reach the waters of Lake Champlain. A stroll along the water is lovely, but if you’re able to snag a boat rental and explore the lake yourself, all the better. At the Lake Champlain Community Sailing Center, it’s $15/hr for kayaks, canoes, and paddle boards, $30/hr for a dinghy, and $60/hr for a keelboat. This is a popular activity, so on hot summer days be prepared to wait for a boat or plan get there before peak hours.
Church Street Marketplace // Nestled in downtown Burlington is an open-air mall lined with shops, cafes, and restaurants, with Church St. being the main drag. In addition to your basic staples (LL Bean, Gap, Athleta, Lululemon, etc) I love stopping into little independent stores like Vermont Flannel Company, Crow Book Shop, and Frog Hollow on the Marketplace. However, one my favorite shops, Common Deer (which features artisan made-in-America goods), is tucked away on College Street, slightly off the beaten path of the main shopping area. In the warmer months there’s also a Saturday farmers market.
Where to Eat in Burlington, VT
Farmhouse Tap & Grill // This farm-to-table Gastropub has one of the best beer menus I’ve ever come across. Whether you visit for brunch, lunch, or dinner, the menu has a little something for everyone.
American Flatbreads // This casual pizzeria is the kind of place that I wish my Boston neighborhood had. On beautiful days, try to snag a seat in the string-light clad outdoor beer garden. The large wood burning oven and red checked tablecloths lend a cozy atmosphere to the inside as well. My favorite pie is the “Revolution,” which has tomato sauce, caramelized onions, mushrooms, cheese, and fresh herbs. (My date raves about the Buffalo Chicken pie.) On a 6-hour road trip from Boston to Mont-Tremblant, Canada, we once pulled off the highway in Burlington and put our names on the list for a table just so we could eat dinner here.
Pizzeria Verita // One can never have enough great pizza places. This Italian restaurant is decidedly more upscale than American Flatbreads, and the romantic atmosphere is perfect for date night. The pizza is deliciously true to the thin-crust Neopolitan style, and the other dishes and specials are delicious too.
Uncommon Grounds // Located in right in the hustle and bustle of downtown Burlington’s Church St., this is my favorite place to get a caffeine fix.
Honey Road // Just when I thought the food scene in Burlington couldn’t get any better, Honey Road opened. This Mediterranean restaurant comes from Oleana alum Cara Chigazola Tobin, and features lots of small mezze meant to be shared (like tapas), rather than large entrees.
Hen of the Wood // If you’re looking for an upscale dinner to celebrate a birthday, anniversary, or the like, this is the spot for you. The farm-to-table menu changes daily, but features beautiful seasonal vegetable dishes, as well as elegant animal dishes that you don’t see everyday (duck, lamb, rabbit, etc.)
Waterworks Food + Drink // Although technically in Winooski, VT, this restaurant is less than a 10-minute drive from downtown Burlington. On par with most Vermont restaurants, the food and beers were superb and locally sourced. But what really drew me to this restaurant was the atmosphere, as it’s housed in an old, textile mill (exposed brick! sky-high windows! Edison light bulbs!) overlooking Winooski Falls.
Where to Stay in Burlington, VT
Hilton Burlington // I have a love-hate relationship with this hotel. This is where I’ve stayed nearly every trip to Burlington. The location is excellent but it’s terribly overpriced (~$275 in peak season) given its lack of charm. However, on the plus side, Hilton Honors members get free parking in the attached garage, and the hotel also has bicycle storage and an indoor pool.
Hotel Vermont // At 4-stars, this hotel is slightly more upscale than the Hilton, and is located right next door. There’s often at least a $30 price difference between the two, which is partly why I haven’t sprung for this hotel yet, but it’s also smaller and tends to book up more quickly. Since it’s relatively new (opened in 2013) I love how nice and clean looking it is. Maybe next time!
Made Inn Vermont // Let me start by saying that I am not a B&B person. I have an aversion to granny textiles and I love the security of being able to call down to a front desk at any hour with room questions or concerns. So I was pleasantly surprised to stumble on this small luxury hotel that happens to be a B&B. The vibe appears to be artsy-chic, and in true Burlington fashion you get a can of Heady Topper upon check-in as a welcome drink. Note that there’s a 2-night minimum during weekends May-October, and prices start at $250/night.
What are your favorite places in Vermont? Anything I should add to my list?