Brattleboro, vermont

Rumor has it that Brattleboro, VT was the inspiration for Justin Timberlake's album, "Man of the Woods", and I believe it. Supposedly, his car broke down on I91 and multiple popstar illiterate good samaritans offered to help him (reminds me of something), and their goodwill made a lasting impression. My fist visit to Brattleboro was nearly 20 years ago and I immediately fell in love. One of my earliest memories is visiting the Brattleboro Farmers Market, a truly unique and delicious experience, watching a group of parents leading their children in some song about drinking cherry wine. It was so over the top cliche and delightful that I knew I'd have to move north one day. And so, here we are (granted I moved to Keene, about 30 minutes from Brattleboro), adding to the cliche of New Yorkers starting over in the country. 

The Basics
Drive Times
Boston, Mass: 2 Hours 
Hartford, CT: 1.5 Hours 
Stamford, CT: 3 Hours 
New York, NY: 4 Hours 
Population
12,046

Where To Stay
Vetted AirBnB's
1. Sunrise Farm, Brattleboro Farm-Stay
Number of Bedrooms: 2
Number of bathrooms: 1
Is it good for families: Absolutely! What a phenomenal opportunity for a family. The property offers a true Vermont farm stay experience but is just minutes from Downtown Brattleboro. The house is quaint, clean, and quintessential New England. The hosts are extremely organized (you can tell just from their write up) and have helpful hints to optimize your stay. You are welcome to experience the farm directly or simply hideaway for a few days, undisturbed. 
How was the host: I met Meghan and she was great. She took me up to the top of the hill of the farm to see the incredible view (views of Mount Monadnock). She loves being an Airbnb host and has really enjoyed the experience. 
Was it clean: Very clean! 
Did it smell?: Not at all. 
Bonus feature: It's 100% a real farm so you can have a truly unique experience. They have a lot of repeat visitors and I am not at all surprised. 

2. Newer Home in the woods, close to everything
Number of Bedrooms: 2 
Number of bathrooms: 1
Is it good for families: Definitely. The listing indicates that it's not appropriate for children under age 2, however. Allie was great and the place is very clean, very organized, and totally clutter free (as some indicate in the reviews as well). Allie and her husband run a printing business as well so there are some really cool works hanging on the walls.
How was the host:  I met Allie and really enjoyed my time with her and the tour of the house. she's takes a lot of pride in the work she's done to maintain and outfit the home and it shows. She was funny and thorough and an excellent host. 
Was it clean: Very clean! 
Did it smell?: Not at all. 
Bonus feature: There is a great area upon entering to drop all your ski gear etc. It's a nice touch! 

​3. Stylish Downtown Retreat 
Number of Bedrooms: 2 
Number of bathrooms: 1.5
Is it good for families: Definitely. It has a fully stocked kitchen and is safe and welcoming. It's located off the main road. It's also colorful and quirky - kids would love definitely love the style and feel the inspiration. Zara (the host) and I had fun discussing our mutual love for Emily Henderson, and you can see that influence in the home. 
How was the host: Zara is wonderful and has added a lot of nice details to the home that make it feel almost like a boutique hotel. There are so many interesting books and she keeps the place extraordinarily clean. She is easy going, informative, and responsive. 
Was it clean: Very clean! 
Did it smell?: Not at all. 
Bonus feature: This home is very close to town and it is possible to walk to town (although might be tricky in the winter). It's also fairly close to the train station which again, is walkable in favorable conditions. 
Extra Bonus feature: The bath tub is awesome. I always love a place that is great for families but also offers a special treat for the parents, and this bath tub is just that! 

4. Brattleboro Vermont Ski Retreat Converted Church
Number of Bedrooms: 3
Number of bathrooms: 2
Is it good for families: It's great for families with kids that are a little older - like ages 5 and up. There are a lot of beautiful ceramics and it would be hard for me to relax there with my 2 year old, for example. 
How was the host: I met Natalie and she is fantastic - warm, engaged, artistic, and definitely safe! 
Was it clean: It was very clean. Natalie and Nick live right next door and so when this space isn't being rented out they use it for events and family. As such, they keep it looking nice and clean. 
Did it smell?:  Not at all. 
Bonus feature: This is a beautiful, interesting, and inspiring Airbnb with something special to offer. It's located in the town of Dummerston, which is just a 10 minute drive to Brattleboro, a great feature for someone who wants to be near action but not smack in the middle of it. 
Extra Bonus feature: Awesome bathroom complete with clawfoot tub and separate, art-tiled, double headed shower . 
Bonus Article: To read more about this property and what to do when in the area, check out this post. 

​Eating and Drinking
Peter Havens: Easily the best restaurant in the Southern Vermont and New Hampshire area, Peter Havens is a must do while in town. Open for dinner from Wednesday through Sunday (and lunch in the summer), chef Zachary Corbin takes his cue from the surrounding farms and culture, providing inspired but unfussy dishes. My favorite (and pretty much everyone's favorite) is the duck entree. 
Duo: Duo is a beautifully designed restaurant - I love the hanging windows and the bar area is full of interesting art work and furniture. The food is solid and reasonably priced. It can be a bit loud (in a good way) and often has live music. 
Whetstone Station Brewery and Restaurant: Incredible views, outdoor dining and drinking, craft beers, and solid pub food make Whetstone Station an excellent choice for casual dining. It does get crowded so I recommend getting there on the early side. 
T.J. Buckly's: Inside a restored 1925 dining car, T.J. serves "New American Cuisine" in a truly unique, fine dining setting. The food is excellent and you must make a reservation in advance. 
Top of the Hill Grill: Back when I was just a visitor to the area, anytime I was in Brattleboro and Top of the Hill was open (it's open seasonally), I insisted on a visit. It is delicious BBQ in a cool setting with both outdoor and indoor seating available. I've eaten here dozens of times and have never had a bad meal. It can be a little hectic, but that's just because everyone wants it! Be sure to check their website to make sure they are open! 
Panda North Chinese and Japanese Restaurant: While I'm typically wary of a mixed Asian bistro, Panda North is the best Chinese and Japanese food around. It's better than most of the Chinese food I had while in New York (the Japanese food of NY has no rival here in New England that I have yet to discover - doesn't mean it's not out there, I just haven't found it). It's a lovely place to dine in or order for take-out. 
Hazel: Hazel has delicious cocktails and on Mondays they offer $5 margaritas (and they are great). They are family friendly but also a nice place to go without the kids. It's affordable casual fare, including pizza, macaroni and cheese, and BBQ dishes. 
Elliot Street Fish, Chips, and More: My sister is always raving about Elliot Street Fish and it's easy to understand why. The fish is really fresh and light, and the coleslaw and tartar sauce are made from scratch in-house. The fish tacos are awesome and I crave them often! It's a relaxed and casual atmosphere that is great for kids. 
Superfresh!: It wouldn't be right to feature a Vermont town and not include the local vegetarian restaurant. Superfresh! is really delicious (and it's BYOB) and offers innovative vegetarian and vegan cuisine and juices. 
Amy's Bakery Arts Cafe: Amy's is a great spot for a quick breakfast or lunch with excellent views. Their Bear Claw might make a you a fanatic, and we won't judge. And if you feel like overindulged, you can always take one of their delicious soups home for a light dinner. 

Shopping
Turn it Up!: ​Turn it up is an independently owned music store (one of 2 locations) that comes complete with incredibly knowledgeable staff that does not outwardly judge your musical taste.  Altiplano: I freaking love this store and typically want to buy everything when I visit. The merchandise is enough of a reason to want to visit Altiplano, but just in case you need more, they support both local artisans and as well as indigenous communities in Guatemala. You'll find truly unique jewelry, clothing, bags, decor, and even toys. I love to even just see their window displays, works of art in their own right. 
Beadniks: When you visit the Beadniks website, they welcome you with "Feed Your Spirit", and I can't think of a more accurate way to summarize what a visit to their store offers. It's a little strange, there's a skee ball machine, toys, clothing, bags, jewelry and thousands and thousands of beads. It's impossible to walk in there and not decide you are going to quick your day job and become a bespoke jewler who lives in this cool town in Vermont, and with their store as inspiration, you might just succeed. 
Penelope Wurr: Another favorite of mine, this store features items for the home, unique baby items, beautiful pajamas, rugs, pillows, glass, jewelry and more. It's a great place to find a great gift for someone you love, including yourself. 
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Art/Museums/Library
Brattleboro Museum & Art Center: The Brattlebro Museum features a rotating roster of exhibitions with the mission to inspire, educate, and provoke its visitors. It doesn't hide from controversial subjects but does manage to always be kid friendly. Admission is $8 for adults and free for anyone under 18, and is free for everyone on Thursdays from 2pm - 5pm. 
Brooks Memorial Library: Let's just start this description by me begging you to not take your local library for granted. The Brooks Memorial Library is one of the best local libraries around and offers a number of free programs. Just because you may be visiting from out of town doesn't mean you can't check out the local library. The Brooks library hosts an event the first Wednesday of every month where notable professors and experts provide free lectures. Want to learn more about Georgia O'Keefe from the former Head of American Paintings at both Sotheby’s and Christie’s? Of course you do! Then make your way to Brattleboro by May 2, 2018. The library offers free crafts for kids EVERY DAY. That's a wonderful thing and a great way to spend an hour working on a project with your little ones.  
Gallery In The Woods: While I love visiting this gallery, I have been having a hard time describing their mission, so I'll let the text from their site do the talking: "Inspired by emerging Visionary artists, and encouraged by the American Visionary Art Museum, we began in 1998 to create  a collection of works in all media from the most simple and direct of craft to the most complex  psycholgical opus. Some artists  prefer to remain unnamed because their sacred art is the work of the collective Spirit, other individuals  have been held in public esteem and have shown their work in museums around the world.  At Gallery in the Woods there exists neither Insider nor Outsider. These works are bonded by the passion of the spirit and the devotion of the studied hand."
Gallery Walk: On the first Friday of every month, Downtown Brattleboro hosts Gallery Walk from 5:30 - 8:30. Galleries and merchants stay open late to welcome visitors with over 20 exhibitions. It's a lot of fun and a testament to the thriving art scene that Brattleboro cultivates.

Nature and Activities
Mount Snow Ski Mountain: A 45 minute drive from Downtown Brattleboro, Mount Snow is the southernmost "Big Mountain" in Vermont. Complete with childcare, ski lessons, tubing (my favorite), lodging, dining, drinking, spa services (at the Grand Summit Resort Hotel on the mountain) and events, it has something for everyone, even the non-skiier who ends up waiting around (ME!). The mountain boasts 86 trails, 600 skiable acres, 20 lifts, and a summit elevation of 3600 feet. 
Granite Gorge Ski Area (both down hill and cross country): A 30 minute drive from Downton Brattleboro, Granite Gorge has something for everyone, including snow tubing, and is also very affordable. Rentals are available and there's a quaint small bar/restaurant with a nice deck for some very low key Apres Ski.  This is a small mountain and it very family friendly. 
Mount Monadnock: About 20 times a day a local Monadnock resident will mention that Mount Monadnock is the most climbed mountain in the world. While it's certainly the most climbed mountain in America, it comes in at a still impressive second for the world. It's a moderately challenging climb and takes a few hours, although legend has it there was a Keene resident who used to climb and descend on his lunch break. So, if you are a hearty New Englander, maybe it's doable in an hour, and for everyone else, I'd budget about 4 hours.  
Madame Sherri Forest: While technically in Chesterfield, New Hampshire, Madame Sherri forest is only a 10 minute drive from Downtown Brattleboro. The forest hosts the ruins of a castle, and pretty much all that remains is a staircase to nowhere (it's as spooky as it sounds). The castle was built in the early early 1900's by a wealthy New Yorker who eventually ran out of money and left the castle to ruin (classic New Yorker). There are numerous trails, some easier than others, so plan your trip accordingly! 
Spofford Lake: A beautiful, 700+ acre lake with one public access beach, Wares Grove, offering a large beach with an extended shallow area (great for the little ones). If you need to break a sweat to work up the courage to actually jump in the water, there's volleyball, basketball, tetherball, playground and a swing set all on site. Naturally, all of this activity will stir up quite the appetite and that's when you can undo all your hard work by hitting up the concession stand. And for all you boaters and paddlers out there, there's also a boat launch. Best of all, as you enjoy wading in the water, take comfort knowing the some George Carlin's ashes were spread here. You're Welcome. 

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