414 Things to Do in Milwaukee's North Shore for 414 Day
Around here, April 14th isn't just another spring day – it's 414 Day! It's a chance to celebrate the spirit of Milwaukee and the communities we call home.
So, in the spirit of 414 Day, we decided to go big. We brainstormed, explored, and maybe got a little carried away, creating a list of precisely 414 things you can do, see, and experience right here in Shorewood, Whitefish Bay, Glendale, Fox Point, Bayside, and River Hills.
Whether you're looking for weekend plans, ways to entertain the kids, free activities to enjoy the outdoors, or just a reminder of how much our local area offers, we hope this list inspires you. Let's celebrate our community – happy 414 Day!
Walk around the peaceful pond in Estabrook Park (Shorewood/Glendale).
Run the paved paths in Estabrook Park.
Visit the Estabrook Beer Garden.
Play a round of disc golf at Estabrook Park.
Have a picnic in Estabrook Park.
Fish along the Milwaukee River in Estabrook Park.
Explore the wooded trails of Estabrook Park.
Visit the Estabrook Park Dog Park.
View the Estabrook Dam remnants/waterfall.
Go sledding in Estabrook Park during winter.
Birdwatch in Estabrook Park.
Walk down to the beach at Klode Park (Whitefish Bay).
Play on the playground at Klode Park.
Have a picnic with Lake Michigan views at Klode Park.
Play tennis on the public courts at Klode Park.
Attend a summer concert event at Klode Park (check schedule).
Enjoy the lake view from the Klode Park bluff.
Fly a kite at Klode Park.
Go sledding at Klode Park in winter.
Hike the ravine trails down to the beach at Doctors Park (Fox Point).
Birdwatch in the wooded areas of Doctors Park.
Go beachcombing along Lake Michigan at Doctors Park.
Enjoy scenic photography at Doctors Park.
Have a quiet picnic at Doctors Park.
Walk the Oak Leaf Trail segment through Kletzsch Park (Glendale).
Run the Oak Leaf Trail segment through Kletzsch Park.
Fish in the Milwaukee River near the Kletzsch Park dam.
Have a picnic in a Kletzsch Park pavilion.
Play on the Kletzsch Park playground.
Visit the archery range at Kletzsch Park.
View the Kletzsch Park waterfall.
Cross the pedestrian bridge over the Milwaukee River in Kletzsch Park.
Hike the trails at Schlitz Audubon Nature Center.
Climb the observation tower at Schlitz Audubon.
Visit the Schlitz Audubon Nature Center indoor exhibits.
Attend an educational program at Schlitz Audubon.
Go birdwatching at Schlitz Audubon.
Go snowshoeing at Schlitz Audubon,
Visit the resident raptors at Schlitz Audubon.
Walk the boardwalks through the Schlitz Audubon wetlands.
Explore the Schlitz Audubon shoreline access.
Walk the Oak Leaf Trail segment in Shorewood.
Bike the Oak Leaf Trail segment in Whitefish Bay.
Walk the Oak Leaf Trail segment in Glendale.
Bike the Oak Leaf Trail segment in Fox Point.
Rollerblade the Oak Leaf Trail in Bayside.
Plan a long bike ride connecting North Shore segments of the Oak Leaf Trail.
Walk along the Milwaukee River in Hubbard Park (Shorewood).
Visit the Hubbard Park Beer Garden.
Reserve a tennis court at Ellsworth Park in Bayside. You can view availability and reserve pickleball and tennis courts, the baseball field, soccer field, and the Ellsworth Park Pavilion.
Stroll across the Hubbard Park footbridge.
Go to the beach at Atwater Park (Shorewood).
Play on the playground at Atwater Park.
Admire the view from Atwater Park's bluff.
See the Francis Hinton statue at Atwater Park.
Play on the playground at Kern Park (Shorewood).
Access the Milwaukee River from River Park (Shorewood).
Play on the playground at River Park (Shorewood).
Play baseball/softball at Cahill Park (Whitefish Bay).
Play on the playground at Cahill Park.
Relax in the green space at Silver Spring Park (Glendale).
Play on the playground at Longacre Park (Fox Point).
Explore the wooded area of Indian Creek Park (Fox Point).
Walk the trails at Indian Creek Park (Fox Point).
Play basketball at an outdoor court in a Shorewood park.
Play basketball at an outdoor court in a Whitefish Bay park.
Play basketball at an outdoor court in a Glendale park.
Play basketball at an outdoor court in Fox Point/Bayside (check Nicolet Rec).
Play catch in an open field at a local park.
Take photos of spring flowers in the parks.
Take photos of fall colors in the parks.
Take sunrise photos over Lake Michigan (Klode, Atwater, Doctors).
Take sunset photos over the Milwaukee River (Estabrook, Hubbard).
Identify different types of trees in the parks.
Try geocaching in a North Shore park. Throughout the North Shore, small hidden caches are tucked in parks and public spaces (check the Geocaching app). There might be one at Doctors Park, or near Atwater’s Bluff, or along the Oak Leaf Trail. Use a GPS-enabled phone to get close, then let the kids’ eagle eyes search for a camouflaged container. Inside might be trinkets to trade. It’s free, it’s exciting, and it will lead you to corners of familiar parks you never noticed before – blending technology, orienteering, and old-fashioned treasure hunting.
Walk your dog (on leash) in designated park areas.
Pack a thermos of coffee/tea for a park bench moment.
Practice yoga or meditation outdoors in a quiet park space.
Go for a mindful walk, focusing on sounds and sights.
Skip stones on Lake Michigan.
Build a sandcastle at Atwater Beach.
Explore Whitefish Bay beaches and build a sandcastle at Klode Beach.
Build a sandcastle at Doctors Park beach.
Watch dogs play at the Estabrook Dog Park.
Find a perfectly shaped skipping stone.
Listen to the waves on Lake Michigan.
Visit a park during different seasons to see the changes.
Sit by the lakefront and simply watch the water.
Go for a walk during a light spring rain (with an umbrella!).
Grab a coffee at Colectivo Coffee (Shorewood).
Grab a coffee at Stone Creek Coffee (Shorewood).
Enjoy pastries at North Shore Boulangerie (Shorewood).
Have breakfast or lunch at City Market (Shorewood).
Eat at Benji's Deli (Shorewood).
Enjoy a meal at Cloud Red (Shorewood).
Have dinner at Oakcrest Tavern (Shorewood).
Visit Harry's Bar & Grill (Shorewood).
Explore wines at Thief Wine Shop & Bar (Shorewood).
Have a drink at The Tap Room (Shorewood).
Watch the Ghost Train roll through the Oak Leaf Trail (Shorewood).
Get your hair cut at The Establishment (Shorewood).
Try MOD Pizza (Shorewood).
Visit Culver's (Shorewood).
Lynden Sculpture Garden (River Hills) – Roam 40 acres of art and nature. Kids can stretch their legs on open lawns dotted with over 50 large sculptures, while parents enjoy the peaceful gardens and pond. Bring a camera for fun family photos with the art.
Grab a bagel at Einstein Bros. Bagels (Shorewood).
Get a sub at Cousins Subs (Shorewood).
Grab coffee at Colectivo near Klode Park (Whitefish Bay).
Grab coffee at Stone Creek Coffee (Bayshore).
Buy bread at Breadsmith (Whitefish Bay).
Enjoy soup and a sandwich at Panera Bread (Whitefish Bay).
Dine at The Bay Restaurant (Whitefish Bay).
Try Yellow Bellies sandwich shop (Whitefish Bay).
Get pizza at Trouble and Sons Pizzeria (Whitefish Bay).
Eat at California Pizza Kitchen (Bayshore).
Have a classic meal at Jack Pandl's Whitefish Bay Inn.
Dine at Moxie Food + Drink (Whitefish Bay).
Order some pizza from Jet’s (Glendale).
Have brunch or dinner at Cafe Hollander (Whitefish Bay).
Get chocolates or ice cream at Kilwins (Bayshore).
Enjoy custard and a burger at Kopp's Frozen Custard (Glendale).
Eat at Noodles & Company (Glendale/Bayshore area).
Get burgers at Five Guys (Bayshore area).
Visit Chick-fil-A (Glendale).
Experience The Bavarian Bierhaus (Glendale).
Dine at Calderone Club (Glendale).
Try a famous butter burger at Solly's Grille (Glendale).
Visit the Sprecher Brewery & Pub (Glendale).
Try J Kols Seafood N More (Glendale).
Get a specialty hot dog at Dr. Dawg (Glendale).
Explore the food court options at Bayshore.
Dine at Pastiche Bistro & Wine Bar (Bayside).
Try Milwaukee Ale House - Grafton (replacement for Libby Montana, near Fox Point/Bayside).
Visit Portillo's for Chicago-style food (Glendale).
Enjoy custard at Gilles Frozen Custard (nearby).
Find a North Shore Friday fish fry at a local tavern, restaurant or church.
Have happy hour drinks and appetizers.
Fishing at Estabrook Park Lagoon (near Shorewood) – Just south of Shorewood’s border, the Estabrook Park pond is stocked for kid-friendly fishing. It’s a beloved nearby outing for North Shore families to teach kids how to fish in a peaceful setting.
Find a restaurant with outdoor seating in the summer.
Get takeout and eat at home.
Get takeout and eat at a park.
Try a new type of cuisine available in the North Shore.
Make a dinner reservation for a special occasion.
Order food online for efficient pickup.
Visit a drive-thru for a quick meal.
Grab a smoothie or juice from The Daily Dose (Whitefish Bay).
Buy Stone Creek Coffee coffee beans to brew at home.
Check restaurant menus online for dietary options.
Community Block Parties – Many North Shore neighborhoods host summer block parties (often in August). If your street has one, it’s a fantastic way to connect – kids play in the (temporarily closed) street, fire trucks might stop by for show-and-tell, and everyone shares potluck dishes. Even if you don’t have one on your block, you can mimic the experience: invite a few neighbor families for a front-yard picnic and water balloon fight. The essence is community bonding, which is at the heart of North Shore living. Sometimes the simplest “event” – hanging out with neighbors – ends up being the most memorable for kids.
Try a seasonal coffee drink at a local cafe.
Try a different flavor at Kopp's.
Enjoy the Estabrook Park Beer Garden atmosphere.
Enjoy the Hubbard Park Beer Garden atmosphere.
Enjoy the Bavarian Bierhaus Biergarten.
Have a family frozen custard taste test (Kopp's vs. Culver's).
North Shore Photo Scavenger Hunt – Create your own photo challenge: list a few iconic local spots and see how fast you can visit and take a family selfie at each. For example, the Shorewood Ghost Train bridge, the Whitefish Bay water tower, the giant cow statues at Kopp’s in Glendale and the fox statue outside Fox Point’s Village Hall. Pile in the car and go snap a photo at each. It’s a goofy way to spend an afternoon, and you’ll end up with a set of memorable family pictures showing off your community.
Have a picnic dinner at Atwater Park watching the sunset.
Visit the WFB Farmers Market to pick out dinner ingredients.
Try making homemade Panera-style soup and grilled cheese.
Bake cookies or brownies together.
Have a themed dinner night at home.
Research family-friendly recipes online together.
Try a new recipe using ingredients from the farmers market.
Plan a week of budget-friendly dinners.
Make coffee at home instead of buying out (most days!).
Shop at the Apple Store in Bayshore (Glendale).
Browse clothing at Bayshore.
Check out Athleta (Bayshore).
Shop at Target (Bayshore).
Visit Trader Joe's (Bayshore).
Explore Total Wine & More (Bayshore).
Browse books at Barnes & Noble (Bayshore).
Window shop along the storefronts at Bayshore.
Relax on the green space at Bayshore Town Center.
Shop for groceries at Sendik's on Silver Spring (Whitefish Bay).
Browse boutiques along Silver Spring Drive (Whitefish Bay).
Visit Winkie's Toys & Variety (Whitefish Bay).
Shop for bikes or gear at Erik's Bike Shop (Bayshore).
Visit the Whitefish Bay Farmers Market (Seasonal).
Run errands at the bank on Silver Spring Dr.
Visit a salon on Silver Spring Dr.
Explore shops on Oakland Avenue (Shorewood).
Buy groceries at Metro Market (Shorewood).
Visit the Shorewood Farmers Market (Seasonal).
Shop for groceries at Pick 'n Save (Fox Point/Glendale).
Use Fitzy’s pharmacy services in Whitefish Bay.
Explore shops at RiverPoint Shopping Center (Fox Point).
Visit a local hardware store (like Winkie's or other independents).
Shop for sporting goods.
Find a unique gift at a local boutique.
Look for deals at Goodwill (Glendale).
Search for other consignment or thrift shops.
Visit a garden center in spring or summer.
Go to the Post Office (Shorewood, Whitefish Bay, Glendale, Fox Point).
Get your car washed.
Buy commemorative stamps at the Shorewood post office.
Send a friend a card via the Whitefish Bay post office.
Shop for greeting cards.
Visit a local jewelry store.
Shop for shoes at Stan’s Fit for your Feet (Glendale).
Buy pet supplies at Hounds Around Town in Whitefish Bay.
Shop for home decor at Mixed Bag in Whitefish Bay.
Get your favorite portrait framed at The Great Frame Up (Whitefish Bay).
Get keys made at Ace (Glendale).
Get a delicious donut at Donut Monster (Whitefish Bay).
Purchase items supporting a local school fundraiser.
Buy spirit wear for St. Monica School.
Buy spirit wear for Whitefish Bay High School.
Buy spirit wear for Bayside Middle School.
Buy spirit wear for Nicolet High School.
Buy spirit wear for Shorewood High School.
Look for locally made products.
Shop after-holiday sales for discounts (budget goal!).
Compare grocery prices between stores (budget goal!).
Plan weekly errands for efficiency.
Visit Bayshore during a weekday for fewer crowds.
Shop the first Shorewood Farmers Market of the season.
Shop the first WFB Farmers Market of the season.
Donate unused items to Goodwill or another charity.
Research accessible activities suitable for varying mobility levels.
See a movie at the Marcus Theatre at Bayshore.
Attend a performance at Shorewood High School (check schedule).
Attend a performance at Nicolet High School (check schedule).
Look for Shorewood Players community theatre productions.
Attend a free summer concert in a park (Klode, Estabrook, etc.).
Find public art installations in Shorewood.
Look for public art at Bayshore.
Admire the architecture of historic homes in Shorewood.
Admire the architecture of homes in Whitefish Bay.
Admire the architecture of homes in Fox Point.
Admire the architecture of homes in River Hills.
Check for local art gallery openings or events.
Listen to live music at a cafe or bar (check schedules).
Attend a school concert at St. Monica School.
Attend the Spring Sing performance.
Attend a school concert or performance at Nicolet High School.
Find out about community band performances.
Learn about the history of Shorewood.
Learn about the history of Whitefish Bay.
Learn about the history of Glendale.
Learn about the history of Fox Point.
Learn about the history of Bayside.
Learn about the history of River Hills.
Visit the North Point Lighthouse (just south of Shorewood) for views.
Attend a lecture or workshop at a library.
Find public art you haven't noticed before.
Take a photo of a historic landmark.
Attend a local festival or fair as a family.
Find a spot to watch 4th of July fireworks.
Attend a local school event or sports game.
Go bowling as a family.
Attend a JCC Summer Camp.
Have a family movie night at Bayshore.
Get popcorn from Trader Joe’s and have a family movie night at home.
Attend a Nicolet High School football game.
Attend a Shorewood High School football game.
Attend Oktoberfest events at the Bavarian Bierhaus.
Attend a community tree lighting ceremony.
Attend a holiday concert or performance.
Watch winter high school sports (basketball, wrestling, hockey).
Attend local dance competitions or recitals.
Watch a local parade.
Attend spring school performances.
Watch spring high school sports (baseball, track, etc.).
Attend the Glendale Root Beer Bash.
Go to an outdoor movie screening at Bayshore.
Decorate your home for Halloween.
Attend a local Trunk-or-Treat event.
Drive around neighborhoods to see holiday lights.
Make a list of North Shore small businesses to support.
Dine at a different locally owned restaurant each month.
Share info about favorite local businesses on social media or with friends.
Visit the Whitefish Bay Public Library.
Check out books from the WFB Library.
Borrow movies or music from the WFB Library.
Attend a program or event at the WFB Library (check schedule).
Use the computers for games at the WFB Library.
Visit the Shorewood Public Library.
Check out books from the Shorewood Library.
Borrow movies or music from the Shorewood Library.
Attend a program or event at the Shorewood Library (check schedule).
Use the computers or Wi-Fi at the Shorewood Library.
Visit the North Shore Library (Glendale).
Check out books from the North Shore Library.
Borrow movies or music from the North Shore Library.
Attend a program or event at the North Shore Library.
Use the computers or Wi-Fi at the North Shore Library.
Check library websites for museum pass programs.
Check program offerings: Whitefish Bay Recreation Department.
Check program offerings: Nicolet Recreation Department.
Check program offerings: Shorewood Recreation Department.
Dog Walks at Carpenter Park (Shorewood) – This small park on Shorewood’s north end (down the bluff from Atwater) is perfect for a quiet walk with the family pup. Enjoy lake breezes and the sound of waves while strolling the grassy area above the beach.
Attend a Shorewood Village Board meeting.
Attend a Whitefish Bay Village Board meeting.
Attend a Glendale City Council meeting.
Attend a Fox Point Village Board meeting.
Attend a Bayside Village Board meeting.
Join a local committee or organization (e.g., park foundation).
Find a local volunteer opportunity that fits your schedule.
Introduce yourself to a neighbor you don't know well.
Take an art class through a Rec Department or local studio.
Take a cooking class.
Learn about the history of your own house or street.
Read a book by a Wisconsin author.
Volunteer together for a short local project (e.g., park cleanup).
Participate in summer reading programs at the library.
Participate in a community clean-up event (Earth Day).
Use the batting cages at Cahill Park (check availability).
Play tennis at the Longacre Park courts.
Go for a scenic run through Shorewood's residential streets.
Go for a scenic run through Whitefish Bay's residential streets.
Go for a scenic run through Fox Point's residential streets.
Go for a scenic run through Bayside's residential streets.
Go for a scenic run through River Hills' quiet roads (use caution).
Use the swimming pool at Nicolet High School (check public hours).
Join a local gym (Anytime Fitness, Planet Fitness, etc.).
Try a class at Orangetheory Fitness (check locations).
Find a local yoga studio.
Find a local Pilates studio.
Visit Fresh Coast Dance studio (Whitefish Bay).
Enroll kids in a dance class at Fresh Coast Dance.
Attend a Fresh Coast Dance showcase or event.
Consider an adult fitness/dance class.
Play tennis at Nicolet High School courts (check availability).
Go rock climbing at an indoor gym (nearby Milwaukee/Brookfield).
Play golf at Lincoln Park Golf Course (Glendale - public).
Inquire about playing opportunities at other nearby public courses.
Go ice skating at the Pettit National Ice Center (nearby West Allis).
Get a therapeutic massage.
Try acupuncture.
Find a local meditation or mindfulness class.
Take a relaxing walk specifically for stress relief.
Try a new running route in a different North Shore neighborhood.
Focus on low-impact cross-training (swimming, biking).
Go kayaking or canoeing on the Milwaukee River (launch points nearby).
Try stand-up paddleboarding on Lake Michigan (rentals nearby).
Join a recreational basketball game or league.
Find a park court for pickup basketball.
Go for a family bike ride.
Walk to a local destination instead of driving.
Stretch regularly before and after exercise.
Find healthy smoothie recipes to make at home.
Family bike ride on the Oak Leaf Trail – Shorewood segment.
Family bike ride on the Oak Leaf Trail – Glendale segment.
Go swimming together at Nicolet Pool.
Try disc golf as a family at Estabrook Park.
Look into running clubs or groups via Rec Depts.
Sign kids up for WFB Rec basketball.
Sign kids up for WFB Little League baseball.
Visit the playground at Klode Park.
Visit the playground at Cahill Park.
Visit the playground at Estabrook Park.
Have a family basketball shootout at a park court.
Go Sledding at Cahill Park.
Visit the library's teen section.
Visit the library's children's/tween section.
Explore Schlitz Audubon Nature Center together.
Have a family board game night.
Great Pumpkin Festival (Whitefish Bay) – Get into the Halloween spirit at Whitefish Bay’s Great Pumpkin Festival. For several nights leading up to Halloween, hundreds of intricately carved pumpkins are lit up in Old Schoolhouse Park, creating a glowing pumpkin patch display. Enjoy live music and hot cider as you wander among the jack-o’-lanterns. You can even carve a pumpkin at home and drop it off to be part of the show. It’s a beloved 30+ year tradition that draws families from all over.
Work on a jigsaw puzzle together.
Attend a free concert in the park together.
Plan a family "staycation" exploring the North Shore.
Create a family scrapbook or photo album (digital or physical).
Go stargazing on a clear night away from bright lights (e.g., lakefront).
Try birdwatching together with a guidebook or app.
Research family-friendly recipes online together.
Live at the Oasis – Glendale’s summer concert series often kicks off with a Stars and Stripes Salute around July 4th and continues on Wednesdays. Each concert has a theme (like “Latin Night” or “Kids’ Concert”). They’re held at the Johnson Controls Outdoor Amphitheater in Maslowski Park, and all are welcome. Bring a picnic or grab concessions from the onsite Sprecher Oasis. It’s a laid-back festival vibe on a weekly basis.
Attend a school concert or performance at Nicolet High School.
Attend a school concert at St. Monica School.
Attend the Spring Sing performance (Whitefish Bay).
Holiday Stroll & Tree Lighting (Whitefish Bay) – The Friday after Thanksgiving, Silver Spring Drive transforms for the annual Holiday Stroll. Bundle up to watch the evening parade complete with Santa and elves, then count down with the crowd as the village tree is lit at Fountain Square. Stores stay open late with cocoa and treats, and you’ll find carolers, live reindeer, and a kiddie train ride. It’s a hallmark event that officially kicks off the holiday season in the Bay
Make homemade pizza together.
Shorewood Criterium Cycling Classic– Feel the thrill of speed at this annual pro bicycle race in late June. Part of the Tour of America’s Dairyland, the Shorewood Criterium brings elite cyclists zooming through Shorewood’s business district on a closed-loop course. Families line the sidewalks to watch; kids bring cowbells to cheer the racers. Some years feature a kids’ fun race too, letting little ones pedal a short stretch of the course. It’s an exciting, high-energy event (and free to watch).
Have a family frozen custard taste test (Kopp's vs. Gilles vs. Culver's).
Attend spring school performances.
Read a book on a park bench at Atwater Park.
Share this list with friends or neighbors for 414 Day!
Visit the Estabrook Beer Garden (Seasonal).
Attend a summer concert event at Klode Park (check schedule).
Go snowshoeing at Schlitz Audubon.
Visit the Hubbard Park Beer Garden.
Visit the Kern Park wading pool.
Watch a Whitefish Bay Little League game at Cahill Park (Seasonal).
Visit the Whitefish Bay Farmers Market (Seasonal).
Visit the Shorewood Farmers Market (Seasonal).
Drive or walk around to see fall colors.
Go apple picking (requires drive outside North Shore).
Go ice skating outdoors if temporary rinks are set up.
Enjoy the Bavarian Bierhaus Biergarten.
Shop the first Shorewood Farmers Market of the season.
Shop the first WFB Farmers Market of the season.
Enjoy the lake view from the Klode Park bluff.
Enjoy the Estabrook Park Beer Garden atmosphere.
Enjoy the Hubbard Park Beer Garden atmosphere.
Take photos of spring flowers in the parks.
Take photos of fall colors in the parks.
Check village websites for specific event calendars regularly.
Find the highest point accessible to the public in the area.
Find the oldest building you can identify.
Write thank-you notes to local service workers or community members.
Set a goal to try 10 new things from this list this year.
Learn to identify 5 local bird species.
Visit all 6 North Shore communities in one day.
Research side hustle ideas compatible with your skills/schedule.
Plan a future day trip starting from the North Shore.
Research local marketing techniques or SEO tips for small businesses.
Practice your photography skills in local parks or neighborhoods.
Map out 5 different running routes in the North Shore.
Plan a week of budget-friendly dinners.
Pack lunches for work/school to save money.
Have a "no-spend" weekend focused on free activities.
There you have it – 414 specific things to do, see, and experience in Milwaukee's North Shore! Happy 414 Day!
In the spirit of 414 Day, we brainstormed, explored, and maybe got a little carried away, creating a list of precisely 414 things you can do, see, and experience right here in Shorewood, Whitefish Bay, Glendale, Fox Point, Bayside and River Hills.