Need a charming small-city getaway near Milwaukee? Head to Waukesha! Nestled in the scenic Kettle Moraine region, Waukesha blends historic charm, vibrant arts, riverside trails, and classic Midwest friendliness. Whether you're walking the riverwalk, discovering art downtown, or enjoying live music in the park, Waukesha is a refreshing and relaxed escape.
Waukesha, WI Highlights:
- For Adventurous Travelers: Hike or bike the Glacial Drumlin Trail – Cruise through wetlands, prairies, and small towns on this scenic 52-mile rail trail.
- For History Buffs: Explore the Waukesha County Historical Society & Museum – Learn about the city’s rich past, including a tribute to guitar pioneer Les Paul.
- For Shoppers: Browse Main Street shops and the Waukesha Farmers Market – Discover antiques, handcrafted goods, local produce, and artisan foods.
- For Couples: Stroll the Fox Riverwalk – Enjoy public art, cafés, and peaceful river views with sunset-perfect seating.
- For Families: Splash around at Springs Water Park – Located at The Ingleside Hotel, this indoor park features slides, pools, and fun for all ages.
When I like to visit Waukesha, WI
The best time to visit Waukesha is from May through October for warm weather, festivals, and outdoor dining. Fall offers crisp air and vibrant colors. Winter is festive with lights, sledding, and cozy shops in historic downtown.
Tips for getting to Waukesha, WI
- By Car: Waukesha is located off I-94, about 25 minutes west of Milwaukee and 90 minutes from Madison.
- By Plane: Fly into Milwaukee Mitchell International Airport (MKE), then drive or take a shuttle to Waukesha.
- By Bus: Waukesha Metro Transit and regional buses offer service from Milwaukee and surrounding areas.
Where I like to stay in Waukesha, WI
- The Clarke Hotel – Boutique hotel in the heart of downtown with Irish-inspired design and walkable access to shops and restaurants.
- The Ingleside Hotel – Family-friendly option with an on-site waterpark, spacious rooms, and easy freeway access.
- Comfort Inn Waukesha – Convenient and budget-friendly option near highways and local attractions.
Best Things to Do in Waukesha, WI
1. Sip Craft Brews at Raised Grain Brewing Company
Raised Grain Brewing Co. is an award-winning brewery in Waukesha, Wisconsin, creating ‘Boldly Brewed Beer’ such as their Kilted Kolsch and Black Walnut Belgian Imperial Stout. Their new Dolphin Tap room is located at the production facility in downtown Waukesha and allows clients great view of the brewery. This great space with high ceiling and lot of repurposed and recycled wood is a popular gathering spot, especially when the brewery rolls out the new brew or there is a game on TV. The kitchen is open from Tuesday to Sunday so plan on pairing your favorite brew with a hand-tossed pizza, brisket sandwich, or our new Wisconsin classic: Brat Bites. . The tours of the brewery are available on Saturdays.
1725 Dolphin Dr Ste B, Waukesha, WI 53186, Phone: 262-505-5942
2. If You Love Live Performances, Catch a Show at Waukesha Civic Theatre
The Waukesha Civic Theatre is a community theater in Waukesha, Wisconsin that offers a range of stage productions in a beautiful historic movie house. The theatre was established in 1957 and its first productions were at Waukesha High School. In 1962 the theatre bought and converted a former church on Washington Street. It was the theatre home until 1999 when the theatre moved to a new facility in the historic downtown Waukesha, the historic PIX movie house. As part of the theatre’s arts education culture, it currently offers year round classes in multiple disciplines. Since the theatre opened in 1957, it has produced or presented over 650 shows, using 14,000 volunteers, entertained 450,000 theatre lovers and educated 15,000 students.
264 W Main St, Waukesha, WI 53186, Phone: 262-547-0708
What to do if you are traveling with kids:
3. Explore the Stars at Horwitz-Deremer Planetarium
Located on the grounds of the Retzer Nature Center, the Horwitz-DeRemer Planetarium is a state of the art planetarium that offers weekend shows for audiences of all ages. The 40-foot dome with 90 theater style seats has a new 4k Digistar system with surround sound speakers. The shows all start with a short tour of the current night sky, a presenter talk and introduction, followed by a full dome planetarium show. The planetarium also offers free sky watching events every first Friday of each month. The planetarium program also serves as a district and community science resource center, introducing fundamental science concepts such as weather, climate, chemistry, physics, and earth science.
S14 W28167, Madison St, Waukesha, WI 53188, Phone: 262-970-4139
Where to Eat:
4. Dine in Style at Tofte’s Table
Opened in August of 2016 in Waukesha, Wisconsin, Tofte’s Table is an upscale eatery with warm atmosphere, colorful walls, luxurious light fixtures and a massive communal dining table that invites sharing and socializing. The place is equally inviting for a romantic dinner as it is for a family lunch or an office party. The food is eclectic, seasonal, using local produce whenever possible and everything is prepared to perfection. Dishes range from everyone’s favorite braised beef short ribs to octopus, grilled and served with greens in a bright lemon-mustard dressing, fried chicken legs with grilled vegetables and chicken and duck thighs with gnocchi and broccolini in the birds’ juices. The bar serves small batch Wisconsin spirits, a variety of craft beer and a curated selection of international wines.
331 Riverfront St, Waukesha, WI 53186, Phone: 262-408-5633
5. Relax with Good Eats and Good Company at The Neighbors Bar and Grille
The Neighbors Bar and Grille in downtown Waukesha, Wisconsin is just what the name says: cozy, friendly neighborhood watering hole and laid-back sports bar with wall-to-wall large screen TVs so you do not miss any game and quirky décor like entire antique motorcycles. The menu is classic pub grub with a twist, with pizzas, sandwiches, soups, burgers and daily specials that include fish and chips and Grilled Prime Rib. There are plenty of games in the back including video poker, arcade games and a jukebox. There is a nice outdoor patio for those warm summer evenings.
s16w22255 Arcadian Ave, Waukesha, WI 53186, Phone: 262-408-5872
6. Savor Local Favorites at Jimmy’s Grotto
Jimmy’s Grotto is a homey, cozy, unpretentious eatery in Waukesha, Wisconsin serving Italian dishes, thin and regular pizzas, Italian sausages and their famous Ponza Rotta. The place has been around since 1946 and many customers come back for the ponza rottas. . Ponza Rotta is a deep fried calzone or folded pizza and it comes, just like their pizzas, with any number of toppings customers desire. It is juicy, greasy, not very health-conscious but absolutely delicious. The menu also includes traditional Italian pastas, sandwiches and appetizers. You can wash it down with beer or sodas. You can buy their ponza rotta frozen and make it at home.
314 E Main St, Waukesha, WI 53186, Phone: 262-542-1500
My favorite local events:
- Friday Night Live (June–September) – Free live music and entertainment on the streets of downtown every Friday evening in summer.
- Waukesha JanBoree (January) – A winter celebration featuring ice sculpting, sledding, fireworks, and more family fun.
- Waukesha County Fair (July) – Classic fair fun with rides, livestock shows, concerts, and deep-fried everything.
My favorite day trips within 30–60 Minutes of Waukesha, Wisconsin:
- Milwaukee (25–30 min) – Explore the lakefront, tour breweries, visit the Milwaukee Art Museum, and enjoy festivals year-round.
- Delafield & Nagawicka Lake (20 min) – Charming small town with boutiques, lake recreation, and hiking trails at Lapham Peak.
- Oconomowoc (30 min) – Enjoy lakefront dining, public beaches, and seasonal events in this lovely lakeside town.
- Holy Hill Basilica (45 min) – Take in panoramic views and explore spiritual serenity at this striking hilltop landmark.
- Old World Wisconsin (35–40 min) – Step back in time at this open-air history museum with costumed interpreters and historic buildings.
Plan Your Trip