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The 6 Essential Weekend Getaways Near Ann Arbor

Weekend trips from Ann Arbor Michigan
Ann Arbor is our favorite place in the entire country and we’re definitely not shy about sharing that, but we all need a little vacation now and again. We think our region’s proximity to some of the country’s and the continent’s most famous landmarks and attractions makes it even better.
Today, we’re helping you nail down your weekend getaway itinerary by sharing the best restaurants, cafés, breweries, museums, hotels, experiences and landmarks in the top six road trip destinations near Ann Arbor. Hop in the car and get ready for a quick trip you’ll never forget!
 
 

Detroit, Michigan

Drive time: 50 minutes | Visit Detroit
Weekend vacation to Detroit, Michigan

Rusted Crow

Where to stay

Detroit Foundation Hotel | Showcasing true Detroit character, this hotel features local collaborations in art, design, food, drink and experiences.
The Inn On Ferry Street | Get the hotel experience in this historic inn featuring four restored Victorian mansions and two carriage houses.

What to eat

Sister Pie | Nontraditional flavor combinations, rustic preparations, local ingredients — you’re going to want one of these pies.
Rose’s Fine Food | As Detroit’s ultimate diner, Rose’s offers made-from-scratch food prepared with top-quality, local Michigan ingredients.
La Feria | This must-try Spanish tapas spot brings a taste of authentic Spain right here to Michigan.
Wright and Company | This dinner destination is run by cocktail expert Dave Kwiatkowski and James Beard award-winning chef Marc Djozlija.
Rusted Crow | This downtown gastro-lounge offers menus of artisan craft cocktails, local beer and American bar eats in a rustic space accented with steampunk decor.

What to do

Baker’s Keyboard Lounge | It has a piano key bar and is the world’s oldest jazz club — you need to go.
Batch Brewing Company | One of Detroit’s best breweries, Batch offers a Feelgood Tap which goes to help Michigan-based nonprofits.
Detroit Institute of Arts | DIA exhibits 65,000 works of art, one of the largest and most significant art collections in the entire country.
Anna Scripps Whitcomb Conservatory | This 982-acre island park located in the Detroit River is the oldest continually-running conservatory in the United States.
Automotive Hall of Fame | Founded in 1939 this museum and hall of fame showcases over 800 worldwide honorees.
 
 

Kalamazoo, Michigan

Drive time: 1.5 hours | Discover Kalamazoo
Weekend vacation to Kalamazoo Michigan

Photo courtesy of Kalamazoo Institute of Arts

Where to stay

The Henderson Castle Inn | This picturesque bed and breakfast is worth the trip on its own!

What to eat

Old Dog Tavern | Offering brunch, lunch, dinner, late night food, free ping-pong and pinball, live music and a neighborhood vibe, this is a must.
Fuze Kitchen & Bar | This downtown dining experience is about art, people and local, seasonal food.
Crow’s Nest | A cornerstone of Kalamazoo culture, you’ll find this eatery in the heart of the historic Vine Street Neighborhood. There’s a reason it’s always busy!
Olde Peninsula Brewpub & Restaurant | Featuring food, cocktails and in-house brewed beers, this was Kalamazoo’s first ever brewpub!

What to do

Black Owl Cafe | This downtown café is home to Kalamazoo Coffee Company and was named Michigan’s best coffee shop by MLive! It’s worth a stop.
Rupert’s Brew House | Located in the historic Oakland Pharmacy building, this bring-your-own-food brewery features handcrafted beers and entertainment five nights a week!
Kalamazoo State Theatre | Originally opened in 1927, this historic theater is Southwest Michigan’s best venue for concerts, shows and entertainment.
Kalamazoo Valley Museum | Offering free general admission, this family-focused museum has exhibits in science, technology and history.
Kalamazoo Institute of Arts | This stunning, nonprofit art museum and school has been exhibiting artworks since 1924. With more than 4,700 fine artworks in its permanent collection, you’ll have plenty to see and plenty to love! 
 
 

Cleveland, Ohio

Drive time: 2 hours, 45 minutes | Destination Cleveland
Weekend vacation to Cleveland, Ohio

West Side Market

Where to stay

The Kimpton Schofield Hotel | This landmark hotel in downtown Cleveland is a great option for a luxurious stay.
Glidden House | Boasting historic charm and luxury boutique style, this is one of Cleveland’s best.

What to eat

Mabel’s BBQ | Renowned chef Michael Symon has developed a BBQ Cleveland can finally call its own.
The Greenhouse Tavern | When Chef Jonathon Sawyer came home to open The Greenhouse Tavern, he brought a local sensibility; he uses only local produce, protein and grains.
SeeSaw Pretzel Shoppe | This casual stop offers just Sawyer’s Signature Bretzels, Sawyer’s Signature Rolls, Sawyer’s Signature Sausage and plenty of craft beer!
Cowell & Hubbard | Zack Bruell reinvented Cleveland’s historic jewelry store and now offers outstanding, upscale food in the turn-of-the-century space.

What to do

Rock and Roll Hall of Fame | Located on the shore of Lake Erie, this national landmark is perfect for music lovers.
Playhouse Square | This downtown theater district is the largest performing arts center in the United States outside of New York.
The Cleveland Museum of Art | Internationally renowned for its substantial holdings of Asian and Egyptian art, this museum, this museum offers free admission to everyone!
A Christmas Story House | If you’ve seen the movie, you need to see the house. You can even stay overnight!
West Side Market | This jaw-dropping market is the oldest operating indoor/outdoor market space in Cleveland and features over 100 vendors.
The Cleveland Orchestra | This 100-year-old venue is one of the five American orchestras informally referred to as the “Big Five”.
 
 

Chicago, Illinois

Drive time: 4 hours | Choose Chicago
Weekend vacation to Chicago, Illinois

Navy Pier

Where to stay

Freehand Chicago | This hostel-style hotel is housed in a historic 1927 building in Chicago’s River North neighborhood.
The Kimpton Hotel Allegro | This boutique hotel shows off the glamour and pageantry of America’s Golden Era in downtown Chicago.

What to eat

Chicago Pizza and Oven Grinder | You have to have deep dish pizza in Chicago and this is one of the city’s best!
Topolobampo | This gourmet spot won the James Beard Outstanding Restaurant award in 2017.
Mortar and Pestle | At Mortar & Pestle, every globally-inspired meal is made by hand with the best ingredients available.
Band of Bohemia | This gypsy-inspired Chicago landmark is the first Michelin-rated brewpub!
The Original Rainbow Cone | This summer destination is home to the layered cone that features orange sherbet, pistachio, Palmer House, strawberry and chocolate ice creams!

What to do

The Art Institute of Chicago | Founded in 1879, this is one of the oldest and largest art museums in the United States.
Navy Pier | This famous landmark is a 3300-foot-long pier on the Chicago shoreline of Lake Michigan.
Millennium Park | You have to snap a photo and prove you were at The Bean!
Chicago Greeter | This free experience pairs you with an enthusiastic and knowledgeable resident for a walking tour of the city!
The Field Museum | One of the largest biological and anthropological museums in the world, this is a great destination for education and for families.
Wrigleyville | Wrigley Field is the centerpiece of this neighborhood. Come through for a taste of Chicago nightlife!
 
 

Mackinac Island, Michigan

Drive time: 4 hours + Shepler’s Ferry | Mackinac Island Tourism Bureau
Weekend vacation to Mackinac Island Michigan

Photo courtesy of Grand Hotel

Where to stay

Grand Hotel | The island’s destination hotel houses eight eateries, including an ice cream parlor, sushi restaurant and tea room.

What to eat

The Pink Pony | Thrillist called this pink-accented, nautical-themed restaurant Michigan’s most iconic bar and grill.
The Chuckwagon | This diner is the locals’ favorite and offers breakfast and lunch in cowboy-inspired diner decor.
Seabiscuit Café | This year-round eatery features an appropriate horse theme from the 1938 true life story of the famous horse, Seabiscuit.
Millie’s on Main | The island’s favorite homestyle pub, Millie’s serves comfort food and cocktails for lunch and dinner.   

What to do

Original Murdick’s Fudge | The home of Mackinac’s famous fudge, you can shop 23 flavors in this charming store.
Fort Mackinac | This namesake fort was built by the British Army during the Revolutionary War.
Mackinac Island Bike Shop | Here, you can rent bicycles to tour the island like a local!
Jack’s Livery Stable | Take a carriage ride through town or learn how to drive the carriage yourself!
Shepler’s Mackinac Island Ferry Cruise | Offering a few of the island’s best lighthouse and night sky views, these trips are an essential excursion.
 
 

Toronto, Ontario  

Drive time: 4.5 hours | Visit Toronto
Weekend vacation to Toronto Ontario Canada

Nathan Phillips Square

Where to stay

The Drake Hotel | This boutique hotel is the city’s epicenter of cool, offering one of the best rooftop terraces in Toronto along with funky dining and cocktail spaces.
Gladstone Hotel | This boutique art hotel 37 unique rooms — each one designed by a different artist!

What to eat

Antler | This hyper-local and hyper-Canadian restaurant offers cocktails and meals, both created using local, seasonal and wild, foraged ingredients.
Rose & Sons | You can come for lunch or dinner any day, but you need to come for weekend brunch.
Patria | This stylish eatery offers authentic Spanish tapas that are as Insta-worthy as the decor.
The Hot House Restaurant & Bar | Since opening in 1994, this has been one of the city’s favorite places for comfort food and live jazz.

What to do

Amsterdam Brewhouse | Though they have three different Toronto locations, the 14,000-square-foot lakeside brewhouse is the best place for patio beverages!
The Distillery District | This historic pedestrian-only neighborhood draws crowds of art lovers, boutique shoppers and foodies.
Massey Hall | This internationally famous venue holds 2,765 guests and hosts the best shows and acts in the country!
Art Gallery of Toronto | With a collection of more than 90,000 works of art, this museum is among the most distinguished art museums in North America.
Ripley’s Aquarium of Canada | One of three Ripley-owned aquariums, Canada’s location houses 16,000 aquatic animals!
Casa Loma | This historic, Gothic Revival home offers decorated suites, secret passages, an 800-foot tunnel, towers, stables and beautiful five-acre estate gardens to explore.
 
 

Safe travels!

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