The best late summer trips in the US include modern cities, lush valleys, and quaint towns, as well as a couple of resort towns over the border. August and September are usually when most destinations bid farewell to the summer crowds, so you’ll enjoy shorter lines at famous landmarks.

    Weather conditions at the end of summer vary greatly, depending on where you are in North America. The good thing is that many of the cities and towns on our list have excellent indoor activities for all ages. You can still enjoy plenty of time in the great outdoors, whether that’s sunbathing on the beach, hiking and camping in national parks, or boating on pristine lakes. Want to catch the last of the summer sun? Plan a trip to our recommended destinations below.


    Las Vegas, Nevada

    Spectacular shows, shops, and casinos

    Las Vegas is fun year-round, though it can get rather scorching if you’re visiting in late summer. The city has plenty of indoor entertainment for all ages, particularly focused around The Strip. This iconic stretch of South Las Vegas Boulevard is packed with luxurious resorts, casinos, theatres, bars, and nightclubs.

    Families can spend hours exploring the Las Vegas Natural History Museum, Madame Tussauds Las Vegas, Shark Reef Aquarium at Mandalay Bay, and Ethel M Chocolates Factory. Adventuredome at Circus Circus Las Vegas offers indoor roller coasters, clown shows, classic rides, and 4D theatres. Head over to the Freemont Street Experience at dusk to enjoy Viva Vision’s dazzling audio-visual displays, which last 6 minutes. READ MORE…


    Orlando, Florida

    Great for family getaways all year round

    Orlando is one of the most family-friendly cities in the US, thanks to world-renowned theme parks at Walt Disney Resort and Universal Orlando. Visiting in late summer usually means smaller crowds and shorter lines for rides. The weather can get rather cloudy, so we recommend carrying an umbrella or raincoat whenever you’re outside.

    There are plenty of fun things to do in Orlando besides its amusement parks. You can enjoy go-karting and arcade games at Andretti Indoor Karting and Games Marietta, or indoor skydiving at iFLY Orlando. If you prefer a leisurely day near Orlando, check out the Kennedy Space Center. This fully operational NASA launch center hosts the original Space Shuttle Atlantis, the Astronaut Hall of Fame, a 3D IMAX theatre, and a launch simulator. READ MORE…


    New York City, New York

    Iconic museums, fun celebrations, and Broadway shows

    A late-summer vacation in New York City usually means plenty of cultural celebrations and Broadway shows. Some of the most popular events in the city include Shakespeare in the Park, Hispanic Heritage Month, and the Armory Show. Alternatively, you can head to the Theater District to enjoy a wide range of performances, from Broadway and stand-up comedy shows to ballet and classical music concerts.

    Museums in New York are filled with interesting displays and activities for all ages. Must-visits include the American Museum of Natural History, Metropolitan Museum of Art, and Whitney Museum of Art. Lastly, end the day with a drink at the city’s rooftop bars, where you can enjoy a nice breeze and spectacular views. READ MORE…


    Chicago, Illinois

    Street art, free concerts, and urban hikes galore

    Chicago is one of the best cities for a late summer trip in the US. Temperatures in August and September are mild enough to enjoy a wide range of outdoor activities. There’s also plenty of free concerts and art exhibitions to enjoy throughout your vacation, including Grant Park Music Festival and Chicago Blues Festival.

    Millennium Park features playgrounds, a splash park, and walking paths, along with futuristic sights like the iconic Cloud Gate and Crown Fountain sculptures. You can enjoy a leisurely boat cruise along the Chicago River or stroll the 18.5-mile-long Chicago Lakefront Trail. There’s also plenty of greenery to explore in Chicago, such as Lurie Garden, Maggie Daley Park, and Grant Park. READ MORE…


    Cancun, Mexico

    Pristine beaches, mysterious cenotes, and Mayan ruins

    Cancun is a great getaway year-round, thanks to its beautiful shoreline, world-class resorts, and historical landmarks. Playa Langosta, Playa Delfines, and Playa Tortugas are great beaches for swimming and sunbathing on. Nature trails, bike rides, jungle tours, and adventure circuits are available for those who want a more active vacation. 

    The El Ray Archaeological Zone and the El Meco Archaeological Site offer a cultural diversion from the beach. It’s also a good idea to check out the cenotes near Cancun. Plentiful in the Yucatán Peninsula, these natural pools contain mineral-rich water and unique rock formations. Most also have diving platforms and walking paths for added convenience. READ MORE…


    Oahu, Hawaii

    Festivities centered around Hawaiian food and heritage

    Oahu gets very lively between August and September when the island hosts several festivals dedicated to the local heritage, food, and music. Aloha Festival is a month-long event that includes fun parades, local cuisine, and Hawaii’s largest street party.

    Even without the festivals, Oahu has plenty of things to do in late summer. It’s quite cool throughout the day, so you can enjoy many outdoor activities without breaking a sweat. Hiking is a great activity, thanks to scenic routes like Diamond Head, Kuliouou Ridge Trail, and Makapu‘u Point Lighthouse Trail. READ MORE…


    Punta Cana, Dominican Republic

    Plenty of fun and variety behind superb sandy shores

    Punta Cana is a prominent resort destination in the Dominican Republic. If you’re visiting towards the end of summer, you’ll have the advantage of small crowds on the beach and relatively affordable accommodation. The weather can be slightly unpredictable though, with chances of storms in September.

    You still can enjoy sunny days in Punta Cana, during which Bavaro Beach, Macao Beach, and Juanillo Beach are great for sunbathing and swimming. On rainy days, pamper yourself with a spa treatment or take part in salsa dancing lessons. There are also plenty of indoor shopping malls if you're looking for a nice memento for your trip. READ MORE…


    Yellowstone National Park, Wyoming

    Dramatic peaks and geothermal landscapes

    Yellowstone National Park covers over 2 million acres, spreading into Wyoming, Montana, and Idaho. The park is a popular destination for outdoor enthusiasts and nature lovers, thanks to its varied landscape and an endless array of outdoor activities. Hiking is a great way to explore Yellowstone National Park’s many natural wonders.

    Must-visits include the Grand Canyon of the Yellowstone River, Grand Prismatic Spring, and Mammoth Hot Springs. Don’t leave out Old Faithful – this cone geyser erupts around 20 times a day, between 100 and 180 ft into the air. It’s a good idea to visit Yellowstone before the start of fall as many park amenities and campgrounds are unavailable from mid-September onwards. Many restaurants surrounding the national park operate at reduced hours, too. READ MORE…


    Napa Valley, California

    Wine tastings and train rides during harvest season

    Napa Valley is busiest during late summer, as the region’s harvest season lasts from August to October. It’s a great time to visit quaint towns like Angwin and Calistoga – both have excellent wineries, historic buildings, and nature trails. However, we highly recommend booking your hotel, wine tastings, and tours well in advance.

    You can hop on the Napa Valley Wine Train for a scenic ride through Wine Country’s gorgeous countryside, lush vineyards, and rolling hills. If you want to escape the crowd, head northeast of Napa Valley to Lake Berryessa. This 20,700-acre lake/reservoir has 2 marinas and 3 recreation areas that rent out kayaks, canoes, and paddleboards. READ MORE…


    Jackson Hole, Wyoming

    A great town for outdoor activities, wildlife spotting, and Wild West fun

    Jackson Hole is a great place for outdoor adventures in late summer when temperatures are significantly cooler throughout the day. Hiking is a must-do at the Grand Teton National Park, where miles of trails meander through mountains and around lakes. Plan your visit in the first 2 weeks of September if you want to scale the Teton Range, especially the 13,770-ft-high Grand Teton peak.

    Jackson Hole offers ample wildlife-watching opportunities throughout the year. It’s home to one of the largest elk herds in North America, as well as bison and grizzly populations. The town of Jackson takes you back to the Wild West with western rodeos, chuckwagon dinners, and reenactments of frontier town justice. READ MORE…

    Penny Wong | Compulsive Traveler

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