10 Gloomiest Cities In The US

Jun 25 , 2022 · 10 min read

Cloudy days are fantastic for staying indoors with hot coffee, going to the movies and shopping at the mall. Don’t dismiss a gloomy day because they can be the best ones ever.

For photography, an overcast day can be much better than a sunny day. Cloudy days make for soft filtered light while harsh shadows form on sunny days, not to mention people squint and sweat more on bright sunny days.

If you are taking photos, a cloudy day is just perfect.

We’ve researched the gloomiest cities in America and while they might have the most cloud cover, they are still epic places to visit.

If you want a vacation that is exciting, fun and inspiring but does not necessarily care about being on the beach or in the sun all day long, these destinations should be on your travel radar.


10 Gloomiest Cities In The US

Top of our list of gloomiest cities in the US is Anchorage. Anchorage comes first with more cloudy days than any other city in the states.

Alaska’s largest city is a culturally significant place to visit, with the Alaska Native Heritage Center and the Chugach, Kenai and Talkeetna mountains being highlights for any visitor.

The outdoors activities are endless, with gold panning, eco-tours, summer dog sledding and rafting being some of the unique experiences to enjoy.

The great outdoors is beautiful in Anchorage and those cloudy days make it easy to stay outside all day long without worrying about getting too much sun exposure.

You can go camping, stay in a hotel or cabin or book a luxury resort and who cares how cloudy it gets.

You will be having fun hiking, swimming, flying and playing on the water in Anchorage. When it’s time to kick back and relax, there are many restaurants, bars, wineries and shops to explore. 


10 Gloomiest Cities In The US

Portland is the biggest city in Oregon and is nestled on the Columbia and Willamette rivers near beautiful Mount Hood.

People go there for the spacious parks, outdoor facilities such as hiking and cycling tracks and rich coffee and brewery culture. It is one of the cities on the gloomy list yet its eco-friendliness and warm hospitality outshine that.

Visit Washington Park to see the Japanese Gardens and Oregon Zoo, which was founded in 1888.

There is also a charming railway running through the zoo that is home to over 1,800 animals, many of which are endangered or threatened species. The weekend markets are always popular with locals and visitors to the town.

Also, sometimes hanging out in the Pearl District, which has a high concentration of coffee shops, will ensure you get your coffee fix.

Portland, like Seattle, is a bit of a coffee destination, so you can expect high-quality lattes and expressos to start your morning and keep you going throughout the day. 


10 Gloomiest Cities In The US

The weather in Buffalo tends to be gloomy quite often, but the natural beauty of the place always shines. It’s a vibrant city with a buzzing art scene covering classic and contemporary eras.

At the Burchfield Penney Art Center (BPAC), you can see many exhibits by impressive artists and concerts, events and performances.

There is a long list of art galleries, museums, studios and artisan shops as well as street murals around the city to delight art lovers.

The food scene is also happening, with famous food critic Michael Stern calling Buffalo one of the great eating cities.

Foodies from all around agree and love the food trails and cuisine crawls that take them all over the city to taste the best of the best. The weather can be grey and overcast sometimes, but nothing else about Buffalo is gloomy. 


10 Gloomiest Cities In The US

Pittsburgh is a modern city in Pennsylvania with much to see and do. From the Carnegie Museum of Natural History to the current Andy Warhol Museum and the Phipps Conservatory and Botanical Gardens, you will be too busy to notice if the weather is a little gloomy.

There is a big sports scene in Pittsburgh, so you might catch a game or visit a sports bar. There is a zoo and aviary for animal lovers and lots of outdoor space with parks and hiking and biking trails if you want to get some exercise.

Shopping galore, markets, amusement parks and spas make this a place for the whole family.


10 Gloomiest Cities In The US

The beautiful city of Cleveland in the state of Ohio is fifth on our list of gloomiest cities in America. The second-largest state has no shortage of interesting sights and activities to enjoy, even when the weather is a little gloomy.

Playhouse Square in the theatre district is where you can catch Broadway shows and local productions. You can also see a giant outdoor chandelier in the world at Playhouse Square, glittering with thousands of crystals.

Other historical gems to visit are the Cleveland Museum of Art, the Museum of Contemporary Art (MOCA) and Franklin Castle.

Don’t miss Little Italy, with galleries and restaurants lining the charming streets. It has been a favorite place of locals and visitors to Cleveland to roam around since it was founded 130 years ago. Often you can see events and performances.

For gamers, The Superelectric Pinball Parlour will make you forget if it’s gloomy outside. So much fun to be had with many old-school games to play. It’s a unique place to spend a few hours during your time in Cleveland. 


10 Gloomiest Cities In The US

Famous for its coffee culture, tech industry and nature, you really have something for everyone in Seattle. While it might not be sunny in Seattle, it will be fun in Seattle.

Explore the mountains and forests if you are a nature lover, go shopping in glitzy malls and designer stores, enjoy great food and listen to some live music while you ignore the gloomy weather you are likely to experience.

Iconic sites include the Space Needle, the Museum of Pop Culture, the Seattle Art Museum (SAM) and the Columbia Center.

When the weather is bad, the Chihuly Garden and Glass will brighten your day. Impressive glasswork by artist Dale Chihuly can be seen in the museum that showcases his work.

The Glasshouse is a highlight with a stunning orange and yellow creation hanging from the roof. You can book a tour and learn all about the Tacoma-born artist and his influence on the art scene.

Get a Seattle CityPASS to save on many tourist attractions and services if you plan to do lots of sightseeing. 


10 Gloomiest Cities In The US

This Washington state has a lot to offer visitors despite it being on the list of 10 gloomiest cities in the US.

If you go there and find the weather isn’t good, you can head indoors to see the Northwest Museum of Arts and Culture to learn about the history of the area, including Native American heritage.

Campbell House is another historical stop where you can take a guided tour of the building that dates back to the 1900s.

If the weather is overcast, a stroll through the scenic Vast Riverfront Park to see the sculptures and take a ride in the cable car with epic views of the spectacular Spokane Falls.

Manito Park with its beautiful botanical gardens, is another lovely outdoor space to get some fresh air. At night the city is humming with bars, entertainment, restaurants and more.

Start with wine tasting in the Cork District or visit a brewery for a tour with drinks. Then go dancing, catch a concert at The Knitting Factory, or hit a casino for some late-night luck.


10 Gloomiest Cities In The US

Ohio state’s capital city is Columbus, a city that is sometimes called gloomy. But nobody there lets a little cloudy weather stop them from having a great time. There are plenty of parks with great trails and river views.

You can get your culture fix at the Columbus Museum of Art and the German Village area is for history lovers who want to learn about the settlers who lived in the old brick houses on display.

Columbus Zoo and Aquarium has an impressive collection of animals and information to educate visitors. Hop along to the North Market Downtown for great food, drink, produce and gifts.

All kinds of food are there, from Polish to Mexican to Greek to Indian and more. Then take a tour of the Ohio Statehouse before a shopping spree at the Easton Town Center.

Your days will be busy in Columbus even if the Weather Man predicts gloomy weather. 

Fort Wayne

10 Gloomiest Cities In The US

This northeastern Indiana city has some gloom, but who cares when it’s such an exciting destination.

Clouds aside, you can visit interesting landmarks like the Embassy Theatre, the Scottish Rite Auditorium and the Lincoln Tower.

The Foellinger-Freimann Botanical Conservatory gives you the warm feels and awesome photos with pretty gardens, tropical surroundings and outdoor areas to explore if the weather holds out.

At the Fort Wayne Museum of Art, you can see American artwork, including paintings and sculptures. There are plenty of animals to see at the Fort Wayne Children’s Zoo, with many parts indoors or undercover.

You can feed the giraffes, bird watch, take rides and talk to the zoo keepers at the non-profit tourist attraction.

When it is time to eat, you have restaurants, cafes, breweries, wineries, and even food trucks to choose from. The Oyster Bar and Bagger Dave’s Burger Tavern are top-notch places to dine. 


10 Gloomiest Cities In The US

Toledo is a lovely Ohio city near Lake Erie. When you go there, you can expect some gloomy days. That is a great time to visit the Toledo Museum of Art and Toledo Zoo and enjoy some cafe time.

Don’t miss the Old West End, which has charming architecture, including Victorian and Georgian buildings and quaint Edwardian homes.

Then wander around the massive Toledo Botanical Gardens that are pretty even on gloomy days when the sun is hiding behind the clouds.

With over 60 acres of land to explore, you can find a lovely spot for a picnic and some selfies.

Swan Creek is another scenic around to walk around. Deer, fox, birds and other wildlife can be seen in the lush park area that has plenty of picnic and rest spots. If you prefer to dine indoors, Toledo has plenty of fabulous restaurants for lunch and dinner.

We highly recommend checking out Mancy’s Steakhouse and The Oliver House, which is the city’s oldest dining establishment. The food and service at both these places is outstanding.

So there you have it, the ten gloomiest cities in the United States. But it’s not all doom and gloom because these places are nice to visit with plenty to see and do. You don’t need to have a perfect sunny day to have fun in the city.

Just ask the people who live in these cities that are classed as gloomy. They will tell you how much they love their home cities.

So if you are thinking of going to Pittsburgh, Buffalo, Fort Wayne, or any of the other places on our gloomiest cities in the US list, just book that ticket and have fun!

On the Trip Support website, you can read all about Trip Support flights and travel services. Our dedicated travel experts are ready to answer your call at #1-855-606-0606.

They are ninjas when it comes to planning epic vacations and will have you on your way to someplace unique in no time.

At Trip Support, we believe travel is for everyone. That is why we created an innovative and flexible Book Now, Pay Later option.

You can buy the air ticket and vacation packages by paying a small deposit and pay off the balance in easy installments. Flexibility and dollar savings are just some of the advantages of flying with Trip Support.

We don’t check credit scores, so this payment Book Now, Pay Later method ensures vacations are possible for everyone.

What could be easier? You can book now and pay later and go to the United States of America with Trip Support. Get your pay later flights to America with Trip Support today!

Trip Support

The face of travel is changing rapidly. We are proudly leading the industry with an innovative and flexible Book Now, Pay Later Flights option. You can buy the air ticket and vacation packages by putting down a small deposit to secure the services and pay the balance in installments.

Flexibility and savings are just some of the benefits of flying with Trip Support.

We have cheap flights to Rye in Colorado. Book your vacation to Rye and many other wonderful places and pay later with Trip Support. Go ahead and get your pay later flight with Trip Support today!


Flight Deals

Having trouble deciding where you want to spend your dream vacation? Don’t worry, we can help you with that too!

As low as $258.46/per installment

As low as $69.34/per installment

As low as $268.45/per installment

As low as $258.46/per installment

As low as $228.72/per installment

Hotel Deals

Having trouble deciding where you want to spend your dream vacation? Don’t worry, we can help you with that too!

Hero Image
Trip Support Flights, Hotels & Vacation Deals

Book with us and save

Secure your flight ticket, hotel reservation, or your vacation trip with a small deposit. No Credit Check Needed.