Brattleboro is an amazing and quirky city, with a vibrant and artistic downtown. On the first pass, you will most likely happen upon Sam’s Outdoor Outfitters and their big red signage. Do yourself a favor and stop in! Sam’s started as an Army/Navy surplus store in 1932, and over the course of three generations of family ownership, has transformed into the area’s definitive purveyor for any and all outdoor adventures. Spread out over multiple floors, hallways, and vestibules, come on in, feel the history, and get ready for your next adventure.

Located just off the exit of Interstate 91, you’ll find the oasis that is the Vermont Country Deli. We mention the proximity to the interstate only in the hopes that you will find the VCD to be just as integral part of your Vermont road trip plans as we always do. Filled with a dizzying array of deli cases, the good folks at Vermont Country Deli offer a smorgasbord of takeout perfection. Make sure you try their famous Mac & Cheese, as well as any of the options on their sandwich board. And if you are able to leave without indulging in at least one of the truly mind-boggling amount of desserts, well then my friend, you have significantly more willpower than I.

On the other edge of town you’ll find Saxtons River Distillery tasting room. Let’s get this out there right away; Saxtons River Barrel Aged Perc, might just be the best damn liquor ever. Strong words, we know - and it might be the extra jolt that comes from Perc’s artisanal roasting methods of the Arabica beans, but we feel confident that you’ll share in our enthusiasm. Bottom line, the tasting room at Saxtons River is a must-stop every time we’re in Brattleboro, and it should absolutely be on your list as well.

You don’t get to be the number one rated restaurant on TripAdvisor by accident. More than 200 5-star reviews all lead to the same conclusion, if you’re looking for the best food in town, you’re heading to Peter Havens. We’re particularly partial to a restaurant that offers escargot, and we’ve got to say, this might be the best we’ve ever had. With an atmosphere that shines, an extremely well-executed menu, and servers that consistently go above and beyond, do yourself the pleasure of having a delightful evening at Peter Havens.

We’re not going to lie, Brattleboro can be a bit sparse with the lodging options. However, now that you know we’re to be trusted, you can rest assured when we tell you the Inn on Putney Road is an absolute dream. Built in the French Baronial style in the late 1920’s, the bed and breakfast is just as showstopping and whimsical on the interior as it is on the exterior. With kind and dedicated innkeepers offering delicious breakfasts every morning, we can think of no better place to call home during your visit to Brattleboro.

If you’re looking for unique shopping experiences, Brattleboro has your back. That creative and artistic spirit that we mentioned really shines through in not only the retail offerings, but more importantly what isn’t offered. With very few national and chain stores in the downtown area, Brattleboro is very proud of their independent and high quality shopping options. Two of our favorites are Brattleboro Books and Twice Upon a Time.

We’re certainly suckers for a good bookshop and Brattleboro Books just makes us feel all sorts of special. Get lost in the towering rows filled with more than 25,000 used and rare book titles and bring home a treasure or two for yourself.

Similarly chock full of unique finds and curiosities, Twice Upon a Time feels like part art installation, part Gradma’s attic, and fully intriguing. Over 10,000 square feet of vintage clothing, collectibles, and antiques; curated and comprised from the collections of more than 100 dealers and 4,000 consignors. Twice Upon a Time is overwhelming in the very best sense of the word. Stop in, explore, and be amazed.

You absolutely need to take the kids and the entire family to Retreat Farm. Get started with the pasture animals where your little explorers get a chance to interact with all manner of farm animals, including a goat playground and the piggery. Next head over to the Forest Playground and get out some energy jumping stumps and building forts, before you find yourself on the Storybook Walk. Featuring a new book each month, the Storybook Walk takes you and your little kiddos along a gorgeous Green Mountain path while racing along searching for the next page of inspiring, and frequently local, story adventures. Now that might seem like a good amount, and you’d be right, except at Retreat Farm, there’s also a Food Truck gathering (be sure to try Dosa Kitchen!), 10 miles of trails and walking paths, a meditative garden labyrinth, and the Grafton Village Cheese & Wine Shop! We love it here, and know that all members of your crew will love it here too.

Right down the street from the aforementioned Vermont Country Deli, be sure to check out the very photo-worthy Creamery Covered Bridge. Closed nowadays to anything but foot traffic, if you’re on the covered bridge hunt, Creamery Covered Bridge is a great starting point in the state.

And while we’ve mentioned what an excellent spot Retreat Farm is for kids and families, the 10+ miles of Retreat Trails are really just an ideal getaway no matter what your age may be. We personally enjoy the hike up to the Retreat Tower, as well as taking in the view from the top of the stairs on the Harris Hill Ski Jump.

Chelsea Royal Diner has been serving up classic diner favorites for decades. Our rec? Grab a seat at a booth and order the Cajun Skillet Breakfast. Make sure you get the house-made Sunflower toast to sop up all the delicious Cajun flavoring and really kick-start your day.

Alternatively, you can always find something amazing to order at the Vermont Country Deli, but we like to keep it simple with their bagel breakfast sandwiches. Plus you know, a dessert or two, because isn’t dessert really the best breakfast anyways?

Hands down, head to TJ Buckley’s. Set in a restored 1925 Worcester Dining Car (what?!) TJ Buckley’s is helmed by Chef/Owner Michael Fuller. Featuring a colorfully stunning, seasonally rotating, French-inspired menu, we can think of no better place to enjoy a romantic dinner in Brattleboro than TJ Buckley’s.

Talk about a great venue - Stone Church is located in a 140-year-old renovated Victorian Gothic church! The acoustics are as unbelievable as the setting is stunning. Catch a rotating array of musicians and events - the lineup here is incredibly eclectic and creative.

If you haven’t reached your fix of local tunes, keep going a bit further down the road until you find yourself at Whetstone Beer Co. Another epic location venue, Whetstone Beer Co. is right on the bank of the Connecticut River and has a ton of scenic seating options. Featuring live music and events almost every night of the week, you can always find a great new band to get down to, while enjoying a great local brew. Local Tip: The burgers here are banging. We’re partial to the Chicken Sandman, which while we know will ruffle a feather or two of the Burger Purists out there, is absolutely spectacular.

We’ve already espoused the virtues of grabbing a bit to eat at Vermont Country Deli, but should you need to hear it again, you’re going to dig it here! Grab a sandwich, take a quick walk down to the covered bridge and enjoy!

Another favorite of ours is Top of the Hill Grill. This Brattleboro BBQ joint dishes out seriously tasty eats in a super casual, yet scenic setting. Grab some brisket and sides, or maybe one of their killer BBQ/Tex-mex wraps and pull up a picnic table to take in the views of the river valley below.

While many places in town are serving up great cocktails, we just really love the vibe and setting at Whetstone Beer Co. You’re not going to be blown off your barseat by avant garde mixology, but the cocktails are strong, fun, and tasty. That’s pretty darn good in our book.

Calling a co-op a gathering spot may seem like a bit of a stretch, but the Brattleboro Food Co-op really does feel like a community hub. So stock up on all the essentials, plus an excellent selection of pre-made and to-go options at the deli, and get in a conversation with some locals. You’re guaranteed to get at least one or two epic recommendations for what to do with the rest of your Brattleboro visit!