Where to Take an Incredible Vacation from Philly This Fall

With plenty of options, it can be tricky to decide where to head for your fall vacation each year. The fall months are an opportune moment to check out some of the best spots in the region and beyond, and from road trips to casino nights to coastal views, living in Philly puts you in easy reach of a diverse range of trip opportunities.

Whether a cruise remains unchecked on your bucket list, or you’ve always wanted to go check out some autumn festivals, there’s something for you. To enjoy an amazing trip from Philly, explore the list below.

Atlantic City, NJ

It’s one wow after another in New Jersey, from waterfalls and wineries to winding rollercoasters and casinos by the sea. Go for lighthouse tours and luxe mountain resorts. Zoos and ziplining. Hike the Appalachian Trail. Saddle up and go horseback riding. Or kick back and savor Portuguese, Thai, Cuban and fusion cuisine. Find your wow at visitnj.org.
visitnj.org | @visit_nj | 609-599-6540

Brampton Inn, Chestertown, MD

 “Fall” into your happy place this autumn! Along the eastern shore of Maryland, you’ll discover beautiful scenery, winding country roads, shimmering waters and the Brampton Inn. It’s a tranquil retreat surrounded by natural beauty, where city dwellers trade city noise for nature’s tranquil melodies.
25227 Chestertown Road, Chestertown, MD | bramptoninn.com | @bramptoninn | 410-8778-1860

Celebrity Cruises

Getting away for a weekend in the Caribbean has never been easier. Celebrity Cruises’ new 3- and 4-night getaways to the Caribbean allow you to escape any weekend of the year for some sun, sand, and crystal-clear water. With four award-winning ships sailing quick, island-hopping journeys, it’s easy to slip away to the tropics for a weekend and celebrate with friends and family almost any time you want.
37156 Rehoboth Ave., Rehoboth Beach, DE | accentontravel.com | @accentontravel | 888-806-2337

Frederick County, MD

Nothing compares to the stunning fall foliage of the Mid-Atlantic, and Frederick County is no exception! Unwind with the whole family at a fall festival or enjoy a scenic drive through a historic Main Street. From the mountaintops draped in autumn colors to picking apples and pumpkins on farms and orchards and cool days on busy downtown streets, there is no shortage of fall fun in Frederick.
151 S. East St., Frederick, MD | @visitfrederickMD |  visitfrederick.org | 800-999-3613

Gettysburg, PA 

Explore magnificent scenery, outstanding dining, craft beverage and farm market trails, outdoor adventure steeped in our nation’s rich history, unique shops, art, and so much more! Rediscover your inspiration in Gettysburg and Adams County, Pennsylvania, just 2.5 hours away from Philadelphia!
destinationgettysburg.com | @destinationgettysburg | 717-334-6274

Laurel Highlands, PA

Fall is the perfect time for a road trip! Did you know the Laurel Highlands was named a top family road trip destination in 2023 by Good Housekeeping Magazine, and USA Today’s readers awarded this region a TenBest designation for stunning fall foliage? The colors are awe-inspiring and the mountain views are endless. Book a cozy cabin or condo today!
golaurelhighlands.com | @go_laurelhighlands | 724-238-5661

Southern Delaware

Your next big moment happens here, where serene landscapes meet vibrant culture. Immerse yourself in  stunning beaches, charming coastal towns, and endless outdoor adventures. Indulge in Culinary Coast™ cuisine, shop tax-free at boutiques and outlet malls, and experience the freshest finds at local markets. Uncover hidden gems and create unforgettable memories with a visit to Southern Delaware today!
827 E Market Street Georgetown, DE |visitsoutherndelaware.com |@visitsouthdel | 800-357-1818