Leland #Mittentrip
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Good Food, Great People, Beautiful Views: Leland

Weekend road trips are some of my all-time favorite trips to take. They’re generally affordable and force you to explore within a three-hour radius of home, which is something we don’t do nearly enough. One of the challenges that is a side-effect of a weekend trip is finding the balance between making the most of the time you have and making sure that you have fun and relax.

This past weekend, my fiance and I had the opportunity to #MittenTrip to Leland, MI where we discovered some pretty awesome (if not tucked away) treasures on our adventure. We didn’t get to do nearly all the things we had planned because there’s just so much Leland and the Leelanau Peninsula has to offer. Below you’ll find our weekend guide, full of suggestions for your next trip up to Leland!


  • Depart from Holland, MI. For most, getting off of work early to go on a weekend trip just isn’t a reality and that’s okay. We began our trip at 5:30 PM, which worked out well as all the traffic had dissipated.
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Naanwhich at Over the Moon. Photo courtesy of Rachell Weeks.
  • Dinner is important. We knew that we weren’t going to make it to Leland before all of the eateries closed for the evening so we made a point to stop somewhere fun as a part of the trip. At a friend’s suggestion, we sought out Over the Moon Rooftop Deck in Ludington, MI. The waitstaff was incredibly friendly and the variety on the menu was almost as impressive as the view.
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Whaleback Inn. Photo courtesy of Rachell Weeks.
  • Arrive at Whaleback Inn. We pulled into the Whaleback Inn around 10 PM. Tina, one of the owners, met us at the main house, checked us in, and gave us a tour of the grounds. We were floored by how beautiful, well-maintained, and accommodating the property was.
  • Drinks were needed. After the drive, neither of us was ready to just go to bed (despite how welcoming it looked), so we headed over to the Bluebird Restaurant & Tavern for a drink. Full of what we concluded must be locals, the bar was delightful and teeming with energy.


Breakfast At The Tribune. Photo Courtesy Of Rachell Weeks.
Breakfast at The Tribune. Photo courtesy of Rachell Weeks.
  • Breakfast at The Tribune in Northport was a great way to start off the day! Boasting a well-rounded menu full of the breakfast classics (but with a much-needed flare), there wasn’t a single thing that sounded (or looked) unappealing. I’d recommend forgoing the usual table seating and insist on sitting at the bar to watch the action in the kitchen. We literally watched our breakfast be prepared from start to finish.
  • In need of a little time in the woods, we took a short drive down the road to Nagonaba Footpath. Although muddy, the trails were manageable and the wildlife was a treat to watch.
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Hiking trip! Photo courtesy of Rachell Weeks.
  • Still full from breakfast, we postponed lunch and made our way to Northport Brewing Company for a flight of beer samples. We were pleased with the service, the atmosphere was splendid with indoor and outdoor seating, and a food truck out back. We honestly could have spent all day just hanging out!
  • We made the drive back from Northport and found the Village Cheese Shanty in Fishtown for a late lunch. Oh my goodness! I have never had such a great sandwich: The pretzel bread, something they’re known for, made for a delicious change, and the Short’s Brewing Company beer helped wash it all down. Now knowing how big the sandwiches are, I would recommend sharing or bringing a cooler!
Sammies From The Cheese Shanty And A Shorts Soft Parade To Wash Them Down! Photo Courtesy Of Rachell Weeks.
Sammies from The Cheese Shanty and a Shorts Soft Parade to wash them down! Photo courtesy of Rachell Weeks.
  • Exploring Fishtown was lots of fun, and it was hard to believe that these small shanties are still functioning as quaint boutiques. One of the most vibrant was Leland Gal, full of fun fabrics designed by the owner, the boutique had an upbeat and energetic vibe.
Leelanau Wine Cellars. Photo Courtesy Of Rachell Weeks.
Leelanau Wine Cellars. Photo courtesy of Rachell Weeks.
  • After being fully educated on all things wine, we drove straight to The Riverside Inn for drinks and a light dinner. If you’re on a budget (like we were) I would recommend setting some money aside to stop here. The food and drinks were wonderful, the waitstaff very knowledgeable, and the view of the river was stunning.
  • With a beautiful evening to enjoy, we made our way back to the Whaleback Inn with a six-pack to sit on the dock.


A Good Read, Some Coffee And The Rain. Photo Courtesy Of Rachell Weeks.
A good read, some coffee and the rain. Photo courtesy of Rachell Weeks.
  • We woke up to rain which spoiled the plan to go on a hike at Pyramid Point, so instead we made our way to Glen Arbor for breakfast at the Leelanau Coffee Roasters. They had an impressive case of baked goods and two different breakfast sandwiches on the menu. Hoping the rain would stop, we sat around reading the paper and drinking coffee.
Photo Courtesy Of Cherry Republic.
Photo courtesy of Cherry Republic.
  • Unfortunately, the rain didn’t stop but that didn’t deter us from finishing the weekend strong. Just down the street from Leelanau Coffee Roasters is Cherry Republic! With samples of cherry chocolate, cherry BBQ sauce and beverages (if you go next door to their tasting room) galore you could leave with a full belly and a happy heart. We left the shop with a bag full of goodies and made our way next door to their bakery to grab a treat for the road.

Weekend trips can be stressful, but they can also be a blast if you make an effort to plan and set aside downtime. Leland was such a beautiful town, full with really awesome people – I can not wait to go back!

Where are your favorite places to visit on the Leelanau Peninsula? Leland is one of our favorites, what are yours?

Special thanks to our sponsors for making our #MittenTrip to Leland possible: VerizonShorts BrewingGreat Lakes Proud, New Holland Brewing, and High Five Threads

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