Great fit if a community run/walk in Cross Plains, featuring a kids' race and supporting park safety, all part of the festive annual Trout Days.

• Fun
• Competitive
• Quirky
• Festive
• For a Cause

Sat, May 2, 2026, 9:00 AM CDT·1 Miles, 5K·Cross Plains, WI

EasygoingRUN

Course · Rolling · Timed race

Great fit if join a patriotic celebration with a scenic 5K, spirited competition, and a costume contest, all while supporting vital local causes.

• Fun
• Scenic
• Competitive
• Quirky
• Festive

Sun, May 3, 2026, 9:00 AM EDT·1 Miles, 5K·Waldwick, NJ

EasygoingRUN

Course · Hilly · Walkers welcome

Great fit if join the Waverly Waddle for a scenic 5K run or 2-mile walk, a beloved community tradition kicking off summer on Mother's Day weekend.

• Fun
• Scenic
• Competitive
• Festive

Sat, May 9, 2026, 9:00 AM EDT·2 Miles, 5K·Waverly, PA

EasygoingRUN

Course · Hilly · Family-oriented

Great fit if a joyful Mother's Day tradition, this all-women 5K and kids' 1-mile offers a scenic course and festive celebration for all.

• Fun
• Scenic
• Festive

Sun, May 10, 2026, 8:30 AM EDT·1 Miles, 3.1 Miles·Ridgefield, CT

EasygoingRUN

Course · Hilly · Family-oriented

Great fit if run or walk a 5K for a cure, enjoy a kids' fun run, and celebrate with a DJ and food trucks in Danville.

• Fun
• Festive
• For a Cause

Fri, May 15, 2026, 7:00 PM EDT·1 Miles, 3.1 Miles·Danville, VA

EasygoingRUN

Course · Rolling · Timed race

Great fit if run a point-to-point 5K from Gulf Breeze to Pensacola Beach, celebrating with a DJ party, free refreshments, and a finisher's medal.

• Fun
• Scenic
• Competitive
• Festive

Sat, May 16, 2026, 8:00 AM CDT·3.1 Miles·Gulf Breeze, FL

EasygoingRUN

Course · Flat · Walkers welcome

Great fit if dust off your windbreaker for a totally rad 90s-themed 5K, blending fitness, fun, and community celebration.

• Fun
• Quirky
• Festive

Sat, May 16, 2026, 9:00 AM EDT·5K·Jacksonville, NC

EasygoingRUN

Course · Flat · Timed race

Great fit if celebrate Ukrainian culture and unity at this special 5K, honoring the symbolic Vyshyvanka shirt and heritage.

• Fun
• Festive

Sun, May 17, 2026, 8:00 AM EDT·200m, 5K·Hollywood, FL

EasygoingRUN

Course · Flat · Timed race

Great fit if a unique mile race and beer relay at a historic brewery, offering a fun challenge and supporting a local historical society.

• Fun
• Competitive
• Quirky
• Festive
• For a Cause

Sat, May 23, 2026, 12:00 PM EDT·1 Miles, 634 Yards·SAINT BERNARD, OH

EasygoingRUN

Course · Mixed · Hilly · Timed race

Why this rating: Mixed surface + hills

Great fit if a long-standing Memorial Day tradition in Upper Arlington, offering multiple distances and supporting local charitable functions.

• Competitive
• Festive
• For a Cause

Mon, May 25, 2026, 8:30 AM EDT·1 Miles, 5K·Columbus, OH

EasygoingRUN

Course · Rolling · Timed race

Great fit if run a certified 5K along a historic Olympic Torch route, cheered by 15,000 parade spectators at the start of the Memorial Day parade.

• Fun
• Scenic
• Competitive
• Festive

Mon, May 25, 2026, 9:28 AM EDT·5K·Camillus, NY

EasygoingRUN

Course · Hilly · Timed race

Great fit if follow the Yellow Brick Road in Oconomowoc for a scenic 5K run or walk, celebrating the magic of The Wizard of Oz.

• Fun
• Scenic
• Competitive
• Quirky
• Festive

Sat, Jun 6, 2026, 8:00 AM CDT·0.5 Miles, 2 Miles, 3.1 Miles·Oconomowoc, WI

EasygoingRUN

Course · Flat · Timed race

Great fit if run for a cause and celebrate community at the Thorp Fun Run, featuring timed races, kids' events, and festive Thorp Dairy Days fun.

• Fun
• Competitive
• Festive
• For a Cause

Sat, Jun 6, 2026, 9:00 AM CDT·3.1 Miles, 6.2 Miles·Thorp, WI

EasygoingRUN

Course · Rolling · Family-oriented

Great fit if embrace the Halloween spirit with timed endurance loops or a family-friendly trick-or-treat fun run, all while dressed in your best costume.

• Fun
• Competitive
• Quirky
• Festive

Sat, Oct 24, 2026, 6:30 PM EDT·2.2 Miles·Dacula, GA

EasygoingRUN

Course · Road · Hilly · Timed race

Why this rating: Hilly road course