How to plan a multigenerational trip to Ann Arbor with a detailed itinerary

When Destination Ann Arbor reached out to me to create a multigenerational trip to Ann Arbor, I jumped at the chance. I was born and raised in Michigan, but hadn’t spent much time in Ann Arbor or at the University of Michigan since my college days. Don’t tell anyone I went to Michigan State up the road.

Since my mom still lives in Michigan, I thought this was a perfect opportunity for us to travel together again. And my daughter and I decided we could do this as a multi-gen girls’ trip.

Every year I bring my children to vacation at my mom and dad’s house, but we’ve never traveled just the girls. In fact, I probably haven’t traveled alone with my mom since she took me to places like Chicago and Grand Rapids on bus trips. 

A multigenerational trip to Ann Arbor was the perfect place to spend time with my mom, who is in her 80s, my daughter, who is in her 20s, and me somewhere in between. 

Why choose Ann Arbor as a multigenerational destination

Ann Arbor is more than just a college town. As home to the University of Michigan, it’s a great place to include your college-age kid and her grandparents on a tour of the area.

However, we knew it had so much more. Our primary objective was to hit the famous Literati Bookstore, but we also wanted a little art, a little culture, great dining, nature, and a historic downtown. 

Ann Arbor is the biggest city in Washtenaw County, and Destination Ann Arbor put together an itinerary that let us see the best of the entire county. 

We enjoyed adorable Gilmore Girls-esque towns, more bookstores than we can count, world-class dining with international cuisines my mom has never tried before, and, of course, a renowned university as a backdrop.

With this itinerary, I recommend a car. Every place was an easy 20-30 minute drive. 

Planning tips for a multigenerational trip

Before planning a multi-gen trip, keep a few things in mind. Similar to planning with multiple families, here’s what I’d recommend. 

Decide on travel style & activities

Especially with multiple ages, figuring out activities and travel style early helps you decide not only what you will do, but where you will go and even where you’ll stay. Are the grandparents active and mobile? Do accessible accommodations and activities need to be considered?

Choose accommodations that give everyone space

Do you need accessible accommodations? In our case, my mom uses a walker, and a handicap-accessible room made her stay much more comfortable. 

Do you want a rental home where everyone has their own bedroom? Or a hotel room with enough space for everyone to have their own bed?

Do something for everyone

When planning a trip that includes anyone other than yourself, you want to make sure you are doing something for everyone. 

The idea of a multi-gen trip is to experience travel in a way that opens your eyes to what the other person enjoys. 

For example, on our trip, I really enjoyed going to bookstores and discovered how much my mom enjoyed it as well. My daughter likes comedy, and my mom got to participate in a comedy show with both of us. 

We picked activities that at least one of us would enjoy, and hopefully everyone gets something out of it.

Decide if every activity will be together

Even if you are picking activities that have something for everyone, not everyone has to do every choice. 

In the case of the comedy show we attended, we gave my mom an out. If she didn’t want to go, she didn’t have to. 

When you are traveling with multiple ages, not everyone can or will want to do everything, so know that every activity doesn’t have to be a magical moment of togetherness.

Plan for Food preferences and allergies

My mom is from an older generation, born and bred in the Midwest. She’s likely never had the opportunity to try Thai food or sushi. 

We planned restaurants that might have more international cuisine but still had something on the menu that she could choose if she didn’t want to be too adventurous.

Be flexible and patient

Finally, make sure your plans allow room to linger longer at a place or skip something entirely. I’m very lucky to be doing this trip with my daughter at the age she is now, rather than when she was younger. 

She knows she has to be patient when my mom doesn’t walk very fast. My mom was flexible and waited for us when an activity became too much for her or when it got too warm. 

Where to stay in Ann Arbor

We stayed at the Vanguard in downtown Ann Arbor, and it turned out to be the perfect location for our girls’ trip. We stayed in an accessible suite with plenty of room to spread out. The suite had:

• a handicap-accessible bathroom that was large enough to fit two wheelchairs in!
• a walk-in shower with a bench to sit down
• two queen beds
• a living room and dining room with a fold-out sleeper sofa
• an additional half bath, so no one had to wait to use the restroom

The beds were comfortable, the room was spacious, and the city view was beautiful. 

The hotel had a bar and restaurant, open for breakfast and dinner. It seemed to be a popular spot for non-hotel guests, too. We had breakfast there on our last day, and my mom already knew she was ordering an omelet. (Something she doesn’t get often at home!)

Parking is a premium in Ann Arbor, especially when the University of Michigan is back in session. The Vanguard had valet parking with an underground garage, so we never had to worry about finding a spot when we returned to our room. 

The valet was also through an app, so we could request our car while still in the room. By the time we made it downstairs, our car was either waiting for us or a short few-minute wait.

How to get around Ann Arbor

Ann Arbor is about a 30-minute drive from the Detroit airport. If you’re arriving from out of state, start there and grab a rental. Or, if you don’t plan to drive and are staying only in downtown Ann Arbor, you can get by with rideshares.

If you’re staying somewhere like the Vanguard, you are close to downtown. Many of the downtown destinations we wanted to visit were within walking distance, at most a mile to a mile and a half away. 

I ventured out one morning on my own for breakfast and found the walk enjoyable as I strolled by some of the most gorgeous old houses.

Ann Arbor and the University of Michigan have been around since the 19th century, and you can feel the historic collegiate atmosphere radiating through the streets. 

If you’re traveling with family that doesn’t mind walking, you can easily get around downtown Ann Arbor. 

That said, my mom has a walker and needs assistance, so even if we were heading to some of the downtown shops, we drove.

As I mentioned, the Vanguard was super easy to get in and out of, and the valet parking made it accessible. You do have to pay for parking in downtown Ann Arbor, but I found the cost to be extremely reasonable for a big city, at about $1 to $1.50 an hour. 

There are also a few parking garages, and at times I dropped my mom and daughter off and drove a block away to park in a garage. Again, the cost was super reasonable.

The other places we visited within Washtenaw County were about a 20- to 30-minute drive away. Places like Dexter and Chelsea have very small downtowns, and it was easy to park and walk around for shopping and dining. Ypsilanti is split into two regions, not very far apart. 

Our Ann Arbor Multigenerational Itinerary

If you’re looking for exactly what you can do in Ann Arbor on a multigenerational trip, this is the itinerary we followed, with a few extra suggestions at the end.

Note: We were driving from Western Michigan. You can easily mix this up if you’re driving from the Detroit area.

Day 1

Start in Chelsea

Chelsea is an adorable town with a beautiful old main street and Victorian homes lining the streets off Main Street. 

I was surprised to learn it’s the home of Jiffy Mixes, with the tall factory as a centerpiece of town. 

Main Street is easily walkable, with a slight downhill/uphill grade; at one end, a train station goes through Chelsea. 

Shop at Serendipity Bookstore

Serendipity Books is beautifully laid out and has all the latest new releases. They have a great selection for their book clubs. The community loves Serendipity Books so much that they participated in a book brigade when the store moved locations. 

And I found something there that I hadn’t seen before. I bought maps of famous books, which is just a perfect theme for The Booked Route. I bought a map of Frankenstein for my daughter and one of Little Women for myself. 

Lunch at The Grateful Crow 

We went to The Grateful Crow for lunch, and it’s dark and moody in the best way. Tall ceilings, black and red walls, paintings, accents, and little touches like a birdcage above the bar. 

The food is a mix of burgers and sushi. I had my mom try the Philadelphia roll for the first time. We also shared a burger with egg, which was also a first for her, and a Michigan cherry salad, which was full of pickled onions and dried cherries.

Check in at the Vanguard

See our notes above about why this worked.

Shop downtown Ann Arbor State Street

We continued our shopping spree in downtown Ann Arbor in the afternoon. We stopped at Literati Bookstore, which I loved, because it was full of new releases, paperbacks, a section devoted just to Michigan, and their famed typewriter in the basement.

They also had a great selection of book-themed gifts. And when they didn’t have a type of book my mom was looking for, they graciously recommended Crazy Wisdom Books around the corner.

We then strolled to Rock Paper Scissors, where I picked up a game for my daughter, TV Shows Described Poorly. This store is full of pop culture and Michigan-themed gifts. There was a massive table dedicated to Gilmore Girls, which was appropriate since it was fall and this was a girls’ trip. I was also obsessed with their wrapping paper, just gorgeous prints on everything. 

We then popped across the street to Cherry Republic. This store originated in Traverse City, home of Michigan cherries, the Cherry Festival, and the largest cherry pie tin. 

I love that they have samples of everything and cherry-flavored foods throughout. My mom got some cherry snack mix, and Gloria and I tried cherry-flavored root beer and cream soda. We took home a few bottles and drank them on the way to the airport. 

Dinner at Connor O’Neills

Connor O’Neill’s is a proper Irish pub. I recently went to a bar I thought was going to be Irish-themed, but it felt like every other bar. In contrast, Connor O’Neill’s has dark wood columns, themed booths like the writer’s seat, and a fully stocked Irish bar. 

Our food was classic Irish fare. We got fish and chips, which was done perfectly, and Gloria had a Reuben with sauerkraut. I had a proper Magner’s cider to go with my Irish food. We really enjoyed the pub and thought it felt very authentic.

Dessert at TeaHaus

The TeaHaus was one of our favorite places, and it sort of surprised me. 

They have dozens of loose-leaf teas available for purchase in a variety of sizes. They also have a full counter where you can buy tea to drink and desserts. I had hazelnut chocolate cream cake. My mother had macaroons. And Gloria had a Japanese soufflé cake, which was very light and flavorful. 

Another thing I liked about this place was that they had no Wi-Fi available, and people were there playing games, drawing, reading, and connecting.

Day 2

Breakfast at Orijin Bakery

This is where I walk to on my own to meet a friend. Orijin Bakery is a delicious little bakery right off of State Street. It has a very classic, modern, maybe even slightly Swedish feel. 

They had massive croissants and scones, and everything was flaky and delicious. 

I got my mother a cherry scone because I know how much she likes cherries, and she really enjoyed it.

I brought back some breakfast items for my mom and daughter, and it was really nice to have a dining table at the Vanguard.

Morning Kerrytown + Ann Arbor Farmer’s Market

Oh, how I wish I lived closer and didn’t fly into Ann Arbor so that I could take home all the beautiful fruits and vegetables in this charming little farmers market. 

This market had custom honeys, maple syrup, and flowers, and beautiful rows of tomatoes, peppers, and apples. It was a nice little walk, and I think if we lived closer, we could have brought more home. 

We also shopped in nearby Kerrytown, and we enjoyed a vintage store and an amazing yarn store. None of us knit or crochet, but it was so lovely to walk through that store and see all the beautiful yarn colors they had; it definitely makes me want to learn. 

This was one of those multi-use buildings, so there was food, pizza, burgers, a café, just an overall great place to hang out, especially after shopping at the farmers market.

Late morning: U-M Museum of Art or Matthaei Botanical Gardens

We went to the Matthaei Botanical Garden. It was a little warmer than usual that day, and my mom didn’t last very long. 

Still, we got to walk through the tropical garden together. She pointed out a lot of the flowers and plants she liked. Since I live in a more tropical area, I could say, “Oh yeah, we have that in our yard,” or “My neighbor grows these,” so it was a nice way to connect. 

This was a beautiful stop for my mom. If you don’t have mobility issues, there are also several miles of trails to walk. The nearby Nichols Arboretum also offers many nature trails suitable for the whole family.

Afternoon Ypsilanti  book shops, Depot Town, downtown district

We went to Ypsilanti and stopped in the Blackstone Cultural Center and Bookstore, where I had a really nice conversation with the owner. He recommended some great Black-authored books. If you’re venturing into black author literature, I like that he had a variety of books. He’s also looking to grow this to be more of an overall cultural center for the community, and I hope that he’s very successful.

Riverside Art Center Ypsi Fine Arts Club 

The Riverside Art Center in Ypsilanti offers a Fine Arts Club on select nights. On the first and third Wednesday, artists present two pieces of original art. You can attend and learn about a new artist displaying their work. The Art Center is also open to explore art on Saturdays from 11 to 21. Check the current exhibits here. 

Evening Depot Town &  Dinner 

The Depot Town area of Ypsilanti was very enjoyable. We shopped at an antique store where I picked up an old copy of an Agatha Christie novel. We reminisced about some of the games and toys in the store and really enjoyed walking through those shops. 

We had dinner at Thompson and Co, and this was some of the best Cajun food I’ve had north of New Orleans. 

I had gumbo, which was perfectly seasoned and preportioned. It was just the right consistency. 

Gloria and my mom split Cajun-style pasta with shrimp. My mom loves shrimp and doesn’t get it at home very often. She really enjoys the fact that when she goes out to eat, she can get shrimp. Cajun style was also a first for her. 

Both my mom and Gloria said they could not possibly have any dessert. Since this restaurant specialized in southern comfort food and, in particular, New Orleans-style food, I felt that we had to get bananas foster.  Of course, wouldn’t you know it, both of them ate their fair share of the bananas foster even though they said they were not hungry for another bite. It was fun teasing them, especially my mom, as she was scraping the bowl once it was empty.

Day 3

Breakfast

We went to Iggy’s Eggies for breakfast and had really great oversized egg sandwiches. It’s a counter-service restaurant. Very small but definitely delicious, flavorful breakfast 

Later, we went to Bun Chai for coffee. Gloria got a matcha, and I got a chai. Since my mother had never had chai before, she was able to try both the chai and the matcha. In fact, once I had had enough of my chai, she finished it, another first for her. 

This place was absolutely gorgeous. It felt very luxurious sitting in Bun Chai. They also have Wi-Fi, and you could tell that a lot of students bring their laptops. They have space downstairs for them to work. It definitely feels like an upscale, accessible college hangout.

Shopping State Street

Our first shop of the day was Nickels Arcade. This is a 100-plus-year-old shopping district off of State Street in Ann Arbor. The building is an open alleyway with a glass-covered ceiling, and you can visit a variety of shops in the arcade.

We stopped at Arcadian Antiques, which has been in operation for over 40 years, and spoke to the extremely pleasant owner. She told us she only has antiques from 1880 to 1930 because that’s the era she likes.

We also stopped at a vintage store in Nickel’s Arcade that had a nice mix of mid-century furniture, clothing, and jewelry. That is where my mom spotted a pair of citrine earrings she didn’t buy at first. Once we went back to the car, she decided she really did want them, so I went back and bought them for her.

Finally, we landed at Dawn Treader Bookshop, a massive, gorgeous collection of used books. Some of the nicest used books I’ve seen: great condition, wide variety of topics. This is where my mom spent most of her book allowance and took home several books. She was very happy.

Lunch at Sava’s

Because we had a great breakfast, a nice coffee, and a chai snack midday, we opted for a late lunch at Sava’s. Sava’s is a contemporary eatery with locally sourced, fresh food. I ordered fish tacos, which I split with my mom, and Gloria got katsu chicken.

We were there when, all of a sudden, all our phones went off, and a tornado warning came in. The rain started pouring, and the wind picked up. Fortunately, we were in the restaurant in the middle of the day, and the staff was super pleasant. We were invited to stay as long as we wanted. There was no rush, and of course they asked if there was anything they could get us, brought us additional water, and let us know we could go downstairs if we didn’t feel safe.

This was the kind of experience you don’t plan for, but it makes for a great story later.

Drive around campus

Once the storm cleared, we drove around the University of Michigan campus, as I wanted to show my daughter the Big House. The Michigan Stadium is the largest college stadium in the country and seats over 100,000 people. 

While we didn’t go inside, you still get a sense of how massive it is from the outside. 

We also walked through the Law Quadrangle, with grand neo-Gothic buildings, beautifully landscaped lawns, and a bit of University of Michigan history. You can see why this is such a well-known, world-renowned university, and why it’s not considered Ivy League is beyond me.

We skipped dinner that day and rested at the hotel in the afternoon.

Comedy Showcase

This was the event I didn’t think my mom would attend.

Ann Arbor Comedy Showcase hosted a comedy bingo. This was bingo two ways. One was a normal bingo card where they read off numbers between sets, and the other was a bingo card with comedy stereotypes. 

It was a really fun way to keep everyone engaged.

This was when I was surprised that my mom came out. She doesn’t always hear very well, and I thought for sure she would want to stay in the room. But I think she was enjoying the girls trip so much that she didn’t want to miss out on anything.

Day 4

We had breakfast at the Vanguard, and this could’ve been my mom’s favorite place to have breakfast. She was looking forward to an omelet all week, another item she treats herself to when traveling.

Visit Dexter

Unfortunately, when we arrived in Dexter, a storm had blown through the day before, and half the town was without power. That said, it is an adorable little town, not very big, perfectly walkable, and has two bookstores to visit.

We did not go to the Fox and the Feather because they were closed due to the power outage. However, the opposite side of the street was open, and so we were able to stop into Courageous Books. It’s a classic bookstore full of new releases, romance, and mystery, with a nice overall selection. 

One thing that stood out was that I picked up a couple of logic puzzle books, which have become one of my favorite pastimes. 

Visit the Dexter Cider Mill

If you’re visiting in fall, the Dexter Cider Mill is a must. Fresh apple cider, apple cider donuts, apple bread, and just about anything else apple you can think of.

This was one of my favorite fall things to do in Ann Arbor.

We picked up some apple cider donuts dusted with cinnamon sugar. Gloria and I got a little riverside bite in with our pints of apple cider and our apple cider donut. I wish I could’ve brought some home to dunk in coffee.

Optional excursions depending on your interest and activity levels

Visit U of M

Especially if you have college-aged or high school children, you could easily turn this trip into a brief college visit and see what the University of Michigan has to offer. We visited the Matthaei Botanical Gardens. We could also have stopped at Nichols Arboretum, the Museum of Archaeology, the University of Michigan Museum of Natural History, or the UM Museum of Art, all of which are big hits. 

In fact, my best friend asked if we were doing the Museum of Natural History, as it was one of her kids’ favorites when they were younger. This would be a great option if you had kids under 10.

Outdoor adventures

If your family is more adventurous or active, there are some fantastic outdoor adventures that you can do in Ann Arbor:

• Kayak down the Huron River
• Go hiking and biking amongst numerous trails
• Golf
• Go fishing
• For younger kids, there are inclusive parks and playgrounds
  

Performing Arts

In addition to the Comedy Showcase, the Michigan Theater and the State Theater offer plays, concerts, and talks. While we didn’t see anything we could attend during our time there, we would have taken in a night at the theater as well.

No discussion of performing arts would be complete without mentioning the Purple Rose Theater, owned by actor Jeff Daniels and offering unique performances, often premieres of new shows.

Wrapping it up

My mom asked if I would remember the Dawn Treader book shop as we were heading home. She had such a great time browsing there that, even though Ann Arbor is a 3-hour drive for her, she wants to go back. 

That’s just one memory we’ll take away from our multigenerational trip to Ann Arbor. I’m incredibly grateful I got to share this with my mom and daughter. It was a chance for Gloria to know my mom better, and for my mom to see how I work and travel.