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Duluth and North Shore, Minnesota 4-Day Trip Itinerary

Duluth and North Shore, Minnesota Trip - May 15, 2026 to May 18, 2026

May 15 - May 18

A rejuvenating long weekend road trip from Winnipeg to Duluth and the scenic North Shore. This itinerary focuses on natural beauty, iconic landmarks, a touch of shopping, and delicious gluten-free dining experiences. Prepare for stunning lake views, charming city exploration, and relaxing drives.

Duluth and North Shore, Minnesota view
1

Road Trip to Duluth & Canal Park Arrival

Friday, May 15
1.1
08:00 - 16:00

Drive to Duluth

Embark on your scenic road trip from Winnipeg, MB, heading south to Duluth, Minnesota.

Enjoy the changing landscapes as you cross the border and journey towards Lake Superior. Plan for a few stops along the way.

Ensure your vehicle is ready for a long drive. Remember to have your passports ready for border crossing. There are several rest stops and small towns along the route for breaks.

From Winnipeg, MB to Duluth, MN

Self-drive by car.

1.2
16:00 - 16:30

Hotel Check-in

Arrive in Duluth and check into your hotel, Hampton Inn Duluth Canal Park, conveniently located near the waterfront.

Settle in and refresh after your drive. The hotel offers amenities like an indoor pool and fitness center if you wish to relax.

1.3
16:30 - 18:00

Stroll Canal Park

Explore the vibrant Canal Park, a lively waterfront area.

Watch ships pass under the Aerial Lift Bridge, browse unique shops, and enjoy the lakeside atmosphere.

Many shops and galleries offer local crafts and souvenirs. This area is very walkable.

1.4
18:00 - 18:30

See Aerial Lift Bridge

Witness the iconic Aerial Lift Bridge in action as it raises to let ships into Duluth Harbor.

Originally built in 1905, it's a marvel of engineering and a symbol of Duluth.

1.5
19:00 - 20:30

Dinner at Canal Park

Enjoy dinner at one of Canal Park's many restaurants.

Look for establishments like Grandma's Saloon & Grill or Fitger's Brewhouse, which often have clearly marked gluten-free options and knowledgeable staff.

Always inform your server about your gluten-free needs. Many Duluth restaurants are accommodating and used to catering to dietary restrictions. Consider calling ahead to confirm GF menus.

2

North Shore Scenic Views & Historic Estate

Saturday, May 16
2.1
09:00 - 12:00

North Shore Scenic Drive

Embark on a beautiful drive along the North Shore Scenic Drive, offering breathtaking views of Lake Superior. Stop at various overlooks and small towns like Two Harbors or Silver Bay.

This drive is especially beautiful in the spring. There are numerous state parks and trails if you wish to do a short hike.

2.2
12:00 - 13:00

Lunch on the North Shore

Enjoy a casual lunch at a restaurant along the North Shore.

Many local eateries offer fresh fish and American cuisine, with options for gluten-free modifications.

Look for cafes or diners that can accommodate gluten-free requests. Fish fry options can often be made gluten-free by requesting grilled fish instead of breaded.

2.3
13:30 - 16:30

Glensheen Estate Tour

Visit Glensheen, the historic Congdon Estate.

This 39-room mansion offers a glimpse into the early 20th-century life of a wealthy family, with intact original furnishings and art.

Tours are self-guided or guided. Check their website for specific tour options and times. Parking is available on-site.

2.4
17:00 - 18:30

Enger Park and Tower

Head to Enger Park and Tower for panoramic views of Duluth, Lake Superior, and the harbor.

Climb the stone tower for the best vantage point and explore the Japanese garden.

2.5
19:00 - 20:30

Dinner in Downtown Duluth

Explore downtown Duluth for dinner.

Many establishments here are adept at handling dietary requests. Consider restaurants with diverse menus or those known for fresh, locally sourced ingredients.

Seek out restaurants that pride themselves on fresh, made-from-scratch dishes, as these are often easier to adapt for gluten-free diets. Always communicate your needs clearly.

3

Lakeside Relaxation & Historic Train Ride

Sunday, May 17
3.1
09:30 - 11:00

Morning at Park Point

Visit Park Point, a long, narrow sand spit that offers beautiful beaches, walking trails, and unique views of the Aerial Lift Bridge and Lake Superior.

It's a great spot for a relaxed morning walk.

Enjoy the fresh air and expansive views. There are public restrooms and picnic areas available.

3.2
11:30 - 13:00

Duluth City Exploration & Shopping

Spend some time exploring more of Duluth's city center or other neighborhoods for local shops and boutiques. You might find unique souvenirs or local artisan goods.

Check out smaller independent shops for distinctive items. If you enjoy vintage finds, there are often antique stores around.

3.3
13:00 - 14:00
USD 40-60 for 2 people

Gluten-Free Lunch Spot

Enjoy lunch at a restaurant known for its excellent gluten-free offerings.

Consider places like Northern Waters Smokehaus for their delicious smoked fish or Sara's Table Chester Creek Cafe for farm-to-table options.

These establishments often have dedicated GF menus or are very knowledgeable about cross-contamination. Always confirm with staff.

3.4
14:30 - 16:20
USD 40-50 for 2 people

Lake Superior & Mississippi Railroad

Experience a historic train journey on the first railroad route into Duluth.

This 6-mile ride follows the beautiful St. Louis River Estuary, offering scenic views and a glimpse into railroad history.

Check their schedule in advance, as operations can be seasonal or specific to weekends. Booking tickets online is recommended.

3.5
18:30 - 20:00
USD 80-120 for 2 people

Farewell Dinner

Savor your final dinner in Duluth.

For a special treat, consider a restaurant like Va Bene Caffe, known for its Italian fare and often accommodating with gluten-free pasta options and beautiful lake views.

Making a reservation is advised, especially for popular spots on a Sunday evening.

4

Departure from Duluth

Monday, May 18
4.1
08:30 - 09:30
Included with hotel or USD 20-30 for 2 people

Breakfast & Check-out

Enjoy a final breakfast at your hotel or a local gluten-free friendly cafe.

Complete your check-out procedures.

The Hampton Inn offers complimentary breakfast, which may have gluten-free options like fruit, yogurt, or eggs. Always inquire about specific ingredients.

4.2
10:00 - 18:00

Drive back to Winnipeg

Begin your return journey from Duluth, MN, back to Winnipeg, MB.

Take in the last views of Minnesota and plan for stops as needed.

Allow ample time for border crossing and breaks. Consider packing some gluten-free snacks for the road.

From Duluth, MN to Winnipeg, MB

Self-drive by car.

This 4-day itinerary for Duluth and North Shore, Minnesota can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.