Where to enjoy the last days of summer
As sweltering days give way to crisp evenings and the crowds start to fade, here’s where you should go to squeeze in some late summer fun.
As late summer stretches into September, the United States comes alive with contrast and color—sunflowers tilt toward golden skies and hiking trails unfurl beneath the beginnings of fiery fall canopies. It’s a season of in-betweens, where sweltering afternoons give way to crisp evenings, and peak summer crowds taper off enough to let the rhythm of a place shine through.
Whether you crave culture, cuisine, celebration, or solitude, late summer offers a rich mosaic of experiences—each shaped by regional rhythms and seasonal delights. Here’s where to go.
Milwaukee, Wisconsin
Wisconsin’s largest city has many names, but one of its nicknames, "city of festivals," rings especially true in summer. In August alone, the city welcomes at least one major multi-day festival each weekend, including Black Arts Fest MKE, Irish Fest, and Mexican Fiesta. If the food, art, music, and dance at those festivals weren’t enough, mid-week madness (in the best way possible) sprawls across downtown’s Milwaukee Night Market through early September.
The 11-day Wisconsin State Fair kicks off on July 31st and, while locals may have different opinions on the music, performances, and farm competitions, just about every Milwaukee native agrees it’s worth going for the cream puffs alone. In late August, the State Fair Park will also host the Snap-on Milwaukee Mile 250 INDYCAR racing event, followed by Milwaukee Comic Con in September.
Milwaukee’s enormous Harley-Davidson Museum hosts weekly motorcycle demo rides every Saturday afternoon through September, followed by a BBQ and Blues concert in the evening. Each Thursday through late September, the museum grounds also transform into an informal motorcycle show called Bike Night, where 500-1,000 bikers arrive for live music, food, and free concerts. Some attendees even arrive to the riverfront museum by boat.
Late summer is also the perfect time to enjoy one of the city’s quintessential outdoor dining experiences. Wash down a Friday night fish fry with a cold craft beer at Lakefront Brewery, overlooking the Milwaukee River. Or, enjoy a floating feast down the river by renting out a pontoon from Milwaukee Duffy Boats and floating over to Brisa Do Mar Mediterranean restaurant.
Indianapolis, Indiana
The Indianapolis school district kicks back into gear on August 4th, meaning many of the top attractions (like the zoo and museums) are less crowded after that point. Additionally, a set of murals created by female artists for July’s WNBA All-Star Game in Indianapolis will be up another six months (only without the All Star Game crowds).
The Children’s Museum of Indianapolis—the largest in the world—quiets down in early August, and considering their extensive indoor and outdoor exhibits cater to tiny tots and teenagers alike, it’s a great pick for any family. It’s also one of the most accessible museums in the country, as there are sensory-friendly areas, and everything from basketball courts to Indy race car tracks are designed to accommodate children in wheelchairs.
Other quieter-than normal attractions include the immersive Indigenous Australian art exhibit at Newfields art museum and the Indianapolis Zoo, which offers sensory-inclusive days and rents wheelchairs, electric carts, double strollers, and wagons.
From August 1-17, the Indiana State Fair, the sixth oldest in the country, comes alive with more than just fair food. Here, you’ll also find free performances by Babyface and Melissa Etheridge, and thousands of youth projects exhibited at one of the largest 4-H showcases in the country. Come August 28-31, head to the fifth-annual BUTTER Fine Art Fair. This equitable art fair is designed to uplift Black artists and hosts performance art, spoken word, fashion, and food. Unlike other art fairs, 100 percent of the proceeds of art sales go directly to the artists.
Saratoga Springs, New York
Just over three hours north of New York City, you’ll find Saratoga Springs, most famous for the Saratoga Race Course, one of the oldest and most prestigious horse racing tracks in the country. The track captivates crowds through Labor Day weekend, but the city is so much more than racing.
Guided walking and trolley tours run daily through September, and from August 3-9, the Turning Point Parade and Festival celebrates the American victory that changed the course of the Revolutionary War. Come September 20-21, Saratoga National Historic Park will host the 250th anniversary of the first Battle of Saratoga.
The 2,300-acre Saratoga Spa State Park sits right in the middle of town, welcoming visitors to hike, bike, play golf, and tube down meandering streams. This enormous National Historic Landmark also has an automobile museum, kids museum, and historical bath complex. Be sure to sample the park’s famous “sulfur” mineral water, some of which comes naturally carbonated right out of the ground. Also located within the park is the enormous indoor-outdoor Saratoga Performing Arts Center, which will host dozens of big-name classical, pop, and rock concerts through September (think Jonas Brothers, Bonnie Raitt, Billy Idol, and Alice Cooper).
While you’ll find plenty of hotels within town, nature-minded travelers may prefer camping or glamping 30 minutes away, where they’ll be closer to sunflower mazes, and blueberry, pumpkin, and apple picking. Within Saratoga, look for the Giant Pumpkin Fest on September 27.
Portland, Maine
Come late summer, salt-kissed breezes carry the scent of spruce and wildflowers into Portland, Maine, where coastal charm meets easy alpine access. Late August and September still offer warm weather but the crowds are far fewer. And, given that September is still within Maine's prime time for new-shell lobster, visitors can enjoy this delicacy (plus locally harvested bluefin tuna and oysters) without having to wait hours for a table.
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While often celebrated for its historic working waterfront, where lobster boats unload the day’s catch just steps from award-winning restaurants plating it up hours later, Portland is more than lobster rolls. Doubling as a launchpad for hikers seeking rugged scenery and peaceful solitude, this seaside city offers easy access to countless outdoor experiences.
Within an hour’s drive, four distinct state parks offer remarkably diverse landscapes, from gentle forest strolls to panoramic summit views. Two top picks are Bradbury Mountain State Park, where marvelous mountain peaks and well-maintained trails receive relatively few visitors and Sebago Lake State Park, which offers coveted lakeside campsites.
Fall lingers gently in Portland, so you can go whale watching, apple picking, and leaf peeping in both August and September. Surrounding forests begin their slow kaleidoscopic turn in mid-September, with peak blooms appearing as soon as late September in northern Maine.
For even more stunning leaf peeping, head three hours north to Acadia National Park, where crimson maples, golden birch, and russet oaks line inland pedestrian and bicycle trails while lighthouses tower over Atlantic Ocean overlooks. Lighthouse enthusiasts may want to visit around September 13 for Maine Open Lighthouse Day, which also coincides with Portland’s PoutineFest.
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