Best Road Trips from Pittsburgh for Each Month of the Year

Updated January 1 2025

Looking for the best road trip trips from Pittsburgh? I’ve got you covered with one road trip for every month of the year.

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Best Road Trips from Pittsburgh for Each Month of the Year
- January
- February
- March
- April
- May
- June
- July
- August
- September
- October
- November
- December

Pittsburgh is a great city, but sometimes you need to escape the grind of everyday. I try to take some kind of trip every month, even if it’s just an hour away. It helps me reset my mind as I experience new things. 

In the over four years I’ve lived in Pittsburgh, I’ve taken a ton of road trips and here are twelve of my favorite places to visit that are driving distance from the Steel City.

Read on for the best road trip from Pittsburgh for every month of the year!

This post may contain affiliate links, which means I earn from qualifying purchases at no additional cost to you. I only recommend things I've tried myself or that a trusted peer has recommended. Thanks in advance for supporting my work! 

January: Laurel Highlands, Pennsylvania

For your January trip, check out the winter wonderland that is the Laurel Highlands area. If you’ve got snow, there’s no better place to explore outside. The Laurel Highlands offers downhill skiing at three different resorts, cross country skiing or snowshoe rentals, and other amazing winter wonderland adventures. Explore the town of Ligonier, which looks like Stars Hollow in Gilmore Girls. Head to Ohiopyle to view the frozen Cucumber Falls and walk behind a wall of ice like you’re a princess from Frozen.

For more information on what to do in the Laurel Highlands, check out my guide to winter activities in the Laurel Highlands!

February: Lebanon County, Pennsylvania 

Swatara State Park’s trails are passable and beautiful in winter, as long as you pack your microspikes. The hike to Bordner’s Cabin is beautiful in the snow and the open air cabin provides a small respite from wind or elements. Aycriggs Falls is beautiful when frozen. If you want to get warm, check out a forging class at The Drunken Smithy. We learned some of the lost art of forging from two best friends who decided to open this unique business together.

You’ll also be able to catch the snow goose migration at Middle Creek Wildlife Management Area. Usually happening every February, this unique birding phenomenon brings visitors to Lebanon County from all over the world. I’d love to go back and see it again as it was truly breathtaking to see these birds.

If you’re willing to road trip a little bit further, you can also check out Crystal Cave in Berks County, which is about an hour away. This unique cave is open all year round and was the first show cave in Pennsylvania.

For road trip tips that apply for long drives and short drives, check out my Cross Country Road Trip Advice (from someone who’s done it twice!)

March: Kane, Pennsylvania

Kane, Pennsylvania is a small town outside of Allegheny National Forest. Its sense of community and fellowship are unmatched. Stay at the Kane Manor Inn and eat at Table 105. You can shop for gear at Field Street Boots for all sorts of outdoor gear. 

Explore the scenic wonders of Allegheny National Forest such as Rimrock Overlook, Jake’s Rocks, and Hector Falls. March is a great time to see the falls because it only runs if there’s been a lot of water (and the snow melt / rainy season helps guarantee chances of water). March is also a less busy season for the town, so you’ll beat any crows and help stimulate a small town economy with your dollars! Win-win for everyone. 

How to spend 24 Hours in Kane Pennsylvania!

April: Hershey & Harrisburg, Pennsylvania 

Head to the Hershey & Harrisburg area in April. Hershey Gardens will be beginning to bloom and you can enjoy it without the crowds. If it’s chilly out, warm up in the butterfly garden. Hersheypark is also a great place to enjoy an adrenaline rush and you’ll skip the summer crowds. 

This is one of the best areas in Pennsylvania for hiking. Check out many of the area’s hiking trails, including the Ned Smith Nature Center and Art Museum, Meet up with fast long distance takers on the AT via Hawk Rock or Peters Mountain or check out any of the area state and local parks.

To plan your trip, here’s my ultimate guide to an outdoorsy weekend in the Harrisburg area!

May: Cleveland and Cuyahoga Valley National Park, Ohio

Spring is an amazing time to visit Cuyahoga Valley National Park. The park’s waterfalls are amazing in spring, so pack your layers (including rain gear) for an unforgettable experience. The Ledges Trail looks otherworldly when covered in fresh green moss. Best of all, May is usually a less busy time for CVNP so you’ll be able to miss out on fighting for parking spots at some of the most popular attractions. 

In Cleveland, check out some of my favorite spots near the city including Flame and Fable, a romance and fantasy bookstore, any of the Cleveland Metroparks, and the classic Rock and Roll Hall of Fame.

I used to live in Ohio, so I have spent a TON of time in Cuyahoga Valley National Park. Check out my guides to CVNP as you plan your trip!
- Best waterfall hikes near Cleveland
- Guide to Cuyahoga Valley National Park
- Best Waterfall in Ohio: Brandywine Falls

June: State College, Pennsylvania

Visit State College, Pennsylvania when school is out of session to have the town to yourself. This is a great place for outdoor adventure, including hiking, paddle boarding and biking. If you go in early June, you might still be able to catch the mountain laurel on hikes like Yost Run in northern Centre County, but late June guarantees better temperatures. 

Here’s my ultimate State College Weekend Itinerary!

July: Annapolis, Maryland

This adorable Maryland town screams all things summer. Get ready to eat crab cakes, paddle, and enjoy outdoor dining! Tour the Naval Academy and get a glimpse of the first years (or “plebs”) in training. Rent a paddle board from Capital SUP.

Choose what level of upscale you want when eating outdoors. Opt for super casual flip flops and jorts with American fare at Boatyard or more upscale dining at Carroll’s Creek. Stay at The Graduate downtown to avoid having to park or Hilton Garden Inn nearby.

Check out my advice for best hikes near Annapolis!

August: Kelleys Island, Ohio

In August head to Kelly’s Island, Ohio for a beach getaway without having to drive six hours to the Jersey shore. This island in the middle of Lake Erie is the perfect laid-back destination and is great for both solo travelers and families.

Stay at Kelleys Island Adventure Resort where you can relax by the pool. Grab a bike or a golf cart to explore the island. If you wanna get in a hike, there’s a bunch of different options. You can also check out the largest glacial grooves in North America.

For more information and to plan your trip, check out my guide to the best Kelleys Island itinerary!

September: Huntingdon County, Pennsylvania

If you don’t want your summer vibes to be over yet, check out the Raytown Lake region in September. Stay at the Lake Raytown resort in a cabin that’s right on the lake. You can drink your morning coffee on the porch with great lake views.

If you’re visiting in late September, catch early fall foliage via the Thousand Steps Trail. If you’re early in September, it’s usually warm enough to still go for a water adventure like kayaking the Raystown branch of the Juniata River or tubing on the lake. Feel like you’re doing some “back to school” shopping at one of my favorite thrift stores, Twice Upon a Time. 

To plan your trip, here’s the best things to do near Raystown Lake!

October: Ann Arbor, Michigan

Live your best fall foliage life in adorable Ann Arbor, Michigan. You can get all of your cozy vibes by eating at one of the area’s amazing restaurants. Make sure to visit at least one of the town’s five bookstores. If you plan right, you can hit all five in a weekend. This great destination is a great place for a work vacation as there are two different coworking spaces. Feel like you’re going back to school as you mingle with University of Michigan students.

Here’s my guide to the best three day weekend in Ann Arbor!

November: Philadelphia, Pennsylvania

Trade one city for another in November. It’s stick season, so skip the outdoors for a weekend away in one of my favorite cities. Head to the Art Museum to run the Rocky Steps and then peruse the collections. Continue your art journey at the Barnes Museum or tackle something weirder at the Mutter Museum. This museum of medical oddities is not for the faint of heart, as there are many organs in jars (I definitely felt a little queasy while perusing but my mom LOVED it). 

If you want something a little more light-hearted, you can also start to get your Christmas market shopping done at the many Christmas markets around the city. Check out the famous Love Park market or head to Center City to the City Hall one, complete with an ice skating rink.  

If you want to get even further away from Pittsburgh, check out my guide to the best flights from Pittsburgh for every month of the year!

December: Cook Forest, Pennsylvania

Check out Cook Forest in the Pennsylvania Wilds for a December getaway. Walking through the Forest Cathedral with snow on the ground is an enchanting experience and you’ll skip all of the summer crowds. If you get a cabin with a hot tub, it’s a great place to relax and unwind either before or after the stress of the holidays. We visited this area for my end of December birthday in 2024 and it was exactly the relaxing weekend I needed before going back to work in January.

Did I miss any of your favorite road trips from Pittsburgh? Let me know in the comments below or send me a DM on socials @torytalkstrails!