Curated travel guides from like minded travelers around the world |: A collection of experiences and thoughtful recommendations that  inspire others to get Ready to Roam.
Ready and Roam / Stillwater, Minnesota

Ready and Roam / Stillwater, Minnesota

Photo Credit:  Moms of Stillwater

Photo Credit: Moms of Stillwater


Best time to GO: Year round, with summer and fall being my favorite.

After two years of sitting on a gift card for a Bed and Breakfast in Stillwater, my husband and I decided to plan a mid-week escape, take in the beautiful weather and enjoy some time alone. I've certainly spent the day in this river town, but never more than an afternoon or a night out. While many people make Stillwater and nearby Bayport a regular excursion with it's scenic riverside location and area history, I wasn't sure it warranted an overnight stay. I found that not only does it have a lot to offer overnight year round, it's easier than I remembered to visit if you only have a few hours. Only 35 minutes from the Twin Cities, Summer is certainly a nice time to sneak away on a day trip but the Winter ice castles and the changing Fall colors on the bluff are equally enjoyable.

Photo Credit: Jenny Javitch,  Downtown Airbnb  Pictured

Photo Credit: Jenny Javitch, Downtown Airbnb Pictured


As one of MN's oldest cities, Stillwater has a rich and vibrant history. The notorious Younger brothers were once held in the cells of the Washington County Courthouse. These violent bandits, loyal to the Jesse James Gang during the American Civil War, were finally apprehended in 1876 in Northfield, MN where the failed robbery is still celebrated today with the Defeat of Jesse James Days festival every September. In addition to being able to tour the courthouse prison cells and the nearby Warden's House Museum, history buffs can dive deeper into the past on-line at Len's Flare Stillwater for an interactive experience that includes photos and audio narrative.

Photo Credit:  Zazzle

Photo Credit: Zazzle


The Sauntry Mansion / website

While Stillwater does have it's share of historic Inns, the only way to really experience this small town is overnight in the home of a local. If you are staying as a couple, The Sauntry Mansion is the best choice. 

House Rentals

On main street downtown you'll find the best new Airbnb option. This impeccably designed, brand-new property has just started taking bookings and will soon offer a second apartment down the hall in the same building. The units can be reserved together to accommodate a family or larger group, and the owners are just wonderful. Another great option within walking distance of downtown is this spacious loft.

Lora Hotel / see pricing through

We've been looking forward to the opening of this 40 room boutique hotel in Stillwater for over a year and s hot on it's heels, opening late September 2018. Having stayed at The Lora over Labor Day, we can attest to the beautiful rooms and classic comforts. Built in the remnants of a brewery, hidden in a cave system, the hotel retains much of the original character and quirky details, and as an added bonus your encouraged to bring your VIP (very important pet) to enjoy the amenities: beds, bowls, toys and treats. While most of the rooms cater to couples, they do offer accommodations with two queen beds, but keep in mind they are interior spaces and window free.

RTip: is to walk the nearby main street steps, for some exercise and a great view. Or walk all 5 historic sets if you have a lot of calories to work off.

The Hotel Crosby / see pricing through

The Hotel Crosby opened late 2018 and while we haven’t stayed there yet, their getting fabulous reviews. There is a rooftop hot tub and its in a great location. Plus contributors love the farm to table Matchstick Restaurant which has incredible small plates.

Photo Credit:  Amy Rae Photo

Photo Credit: Amy Rae Photo

Photo Credit:  Lora Hotel

Photo Credit: Lora Hotel

Main Street Airbnb. Photo Credit: Jeremy Dallek,  Seamless Media .

Main Street Airbnb. Photo Credit: Jeremy Dallek, Seamless Media.


Brewery Hopping

Our favorite afternoon activity is brewery hopping. Start on the outdoor waterfront patio at Maple Island Brewing, where the El Coronel food truck is permanently parked on Thursdays & Fridays and there is root beer on tap for the kids. Don't leave without a taste of the MIB Bock which is made with 100% pure Wisconsin maple syrup. Afterwards, make your way by car to Lift Bridge Brewing Co, a few minutes drive outside of downtown. This authentic tap room is open year round until 10pm and offers public tours on the weekend. A flight plan of six allows you to sample something new and enjoy fan favorites, Farm Girl Saison and the Getaway Pilsner. Lift Bridge offers events daily, live music often, yard games and picnic tables outside when it's nice out, and piles of unusual board games to pass the time.

Outdoor Sports

My other suggestion for exploration in Stillwater would be to rent paddle boards from 45 Degrees and head to Square Lake Park where there is a boat launch, a fishing pier and a sandy bottom swimming beach. This lake is considered the clearest and cleanest lake in the seven county metro. If you are visiting in the Winter, 45 Degrees also provides trail maps and rents both XC skis and snowshoes.

Another option is kayaking or paddle boarding with Diro Outdoors, where they can also hook you up with camping and bike rental. The completion of the new St. Croix Crossing Bridge in 2017 left the city with less traffic and more opportunities for city and mountain biking, and we are excited for the historic Liftbridge to reopen as a bike and pedestrian passageway in spring 2020.

If you want to take a hike a little off the beaten path, Fairy Falls Trail is a hidden, secret treasure, that is soon to get some love and attention. Residents of Stillwater applied and won a grant devoted to enhancing and maintaining the 60-acre waterfall area and hiking trail.

Photo Courtesy of Diro Outdoors

Photo Courtesy of Diro Outdoors

Photo Credit:  Lori Evert

Photo Credit: Lori Evert


Pinch and Rub / website

The best shopping can be found within a couple blocks of Chestnut and Main downtown. One highlight being the spice and tea vendor Pinch and Rub, where you can taste and smell everything before making a purchase. I recommend the bacon sea salt and the bloody mary seasoning. 

Mara Mi Store + Studio + Cafe / website

Mara Mi is a great spot to sip on a late afternoon chai latte while browsing the affordable infinity scarves and gorgeous stationary.

Modern Roots / website

Don't forget to pop down to MN based Modern Roots for an incredible selection of natural soaps, essential oils and bath bombs that actually lather.

Jori & June / website

With a second location in Illinois, this new clothing boutique is adorable. The brands are what you'd expect from an on-trend shop, the selection is not overwhelming (scarves, sweaters, jewelry) and the staff stylists are super knowledgeable and kind.

Photo Credit:  Mara Mi

Photo Credit: Mara Mi

Modern Roots

Modern Roots

Jori & June

Jori & June


You may not expect that staying in a bed & breakfast allows for enough opportunity to eat out. However, if you don't clean your plate, share lunch or eat smaller meals throughout the day, you will have room to sample the local fare.

Chilkoot Cafe / website

Although there is no table service, the Chilkoot Cafe still feels like a neighborhood chef run restaurant. The staff is super attentive, both beer and wine is offered, and everything is made to order. I'd steer you to the corned beef Reuben and Thor's smoked hot pepper Imperial Porter from Hammer Heart Brewery in Lino Lakes. Trust me, you'll be back again to try something else tomorrow.      

RTip: Before you drive away, walk across the street to Hannah's Homemade Heavens and purchase a few cookies for later.

Phil's Tara Hideaway / 651.439.9850

On your way into town, you must visit the historic landmark Phil's Tara Hideaway for the incredible Mediterranean cuisine and charming dining room. With it's storied past and it's welcoming staff, this spot is a must for a Gyro platter and whatever homemade soup Phil has made that morning. A reservation is suggested in the evening but they are also open for lunch.

Lolo American Kitchen / website

If I have to pick one place to eat in downtown Stillwater, this is it. The burger and fries is a great choice among other great choices, including pork belly tacos and butter poached lobster tails. They don't take reservations but they do use the nowait app.

Pearl and the Thief / website

This Southern whiskey and oyster bar is new downtown Stillwater, and worth a stop for sure. The oysters are top notch and mostly East coast, which is my favorite. The craft cocktails were excellent.  I had an old fashioned that was delicious and my husband enjoyed, "I drink and I know things" - another Bourbon drink, but it seemed lighter and would be my next choice had I ordered more than one. Our preference would be to sit upstairs because the lounge area is so cozy. Everyone said to get the Tennessee hot octupus and while it was good, I wouldn't probably order it again. The fish and chips was literally a whole red snapper and so tasty.

RTip: afterwards go grab ice cream at the walk up window outside Leo's

Photo Credit:  Chilikoot Cafe & Cyclery
The Pearl and the Thief

The Pearl and the Thief


The American Legion / website

Unfortunately many of the waterfront establishments don't serve drinks in glassware when you want to be seated outside, one exception being The Dock Cafe. For anyone over 30 this can be a deal-breaker, but don't worry. Just walk a couple blocks up Myrtle to The American Legion, where you'll find a great Bloody Mary in an actual pub glass. There is space to breathe, and quite a view as you're perched high above main street on their large outdoor patio. Fridays in the Summer, it's the place to be for their fabulous fish fry and pull tabs.

No Neck Tony's / website

Speaking of bloody mary's, I'd be remiss not to mention the award winning version at No Neck Tony's, which if you like a meal in a glass will not disappoint.

The Velveteen / website

Don't leave downtown without checking out Stillwater's throwback underground speakeasy, The Velveteen. With it's big city atmosphere and small town affordability you can't go wrong. As expected it's hard to find, so look for the letter V and the words "follow the rabbit" etched into the concrete out front. You won't regret seeking this place out once you've tasted the Slone Ranger's smoky spice. 

American Legion Stillwater

American Legion Stillwater

Photo Credit:  The Velveteen Speakeasy


Anytime you are visiting a small town there is something about it that feels very reminiscent of being home and we've certainly learned to pack that way. Always including a bottle of wine from our favorite wine club, Sipbetter and grabbing slippers and a Kindle for our overnight bag. We also pack comfy sneakers, and walk hands-free with a belt bag.


Next time we'll take in residential architecture on the South Hill Walking Tour or plan our trip to correspond with the annual Historic Homes Tour in early October.


Click here to see all the places we checked out.

Roam 2 Ways / Washington D.C.

Roam 2 Ways / Washington D.C.

5 Midwest Campgrounds

5 Midwest Campgrounds