2 In Travel

5 East Coast Road Trips to Take This Fall

The 5 Best East Coast Road Trips for Fall via

As much as I hate to admit it, my favorite season is officially winding down today {#summerbaby4ever}. Luckily, early fall on the east coast isn’t too shabby either. We have one big trip planned, which I’ll be sharing more about soon. But other than that, our fall weekends are pretty open, which means… east coast road trips!

The accessibility of so many different cities, geographies and and activities is one of my favorite parts about being back on the east coast. When we lived in Denver, there was plenty to do but the concept of crossing four states in one drive just didn’t exist. I also grew up taking day-long drives between my hometown and our vacation home in Maine, so I experience a nostalgic reverie about road trips, too.

With more than three decades of east coast adventuring, I thought I should collect my top 5 east coast road trips, specifically for fall. All of these destinations are notable in their own right, but admittedly, my list would have a few more beaches for summer and fewer northern destinations in the winter.

So let’s go for a ride, shall we?

The 5 Best East Coast Road Trips for Fallvia

1. Annapolis, Maryland

Why: This is a plug for my hometown, but also a pretty central destination that can’t be overlooked in terms of fall activities & beautiful scenery. If you’re coming from the north, take the scenic route against Waze’s recommendation, down Rte 301. Because nobody really wants to see the NJ Turnpike again and it’s worth the handful of extra miles you’ll travel.

What to Do: Take a walk through City Dock / Ego Alley in downtown Annapolis and grab ice cream at my favorite local spot, Storm Brothers. Ogle a little at the midshipmen {just kidding… sort of} or take a tour of the Naval Academy. Have a crab feast on the water at Mike’s Crab House. Drive over the Bay Bridge and hit up the outlets in Queenstown for deals on fall staples.

Even more info here.


2. Portsmouth, NH

Why: I’ve only really spent time here in the summers with my family but there’s something about coastal New England towns that just make sense in the fall. There’s so much charm to a town that’s been around since the 1600’s and it would be so picturesque as the leaves start to change!

What To Do: Explore the small shops and boutiques in Market Square, maybe even get a head start on holiday shopping {dare I say it!} with some quirky or unique finds. Stop by a coffee shop like Breaking New Ground for a warm beverage to keep you fulfilled while you wander the waterfront, Prescott Park. Even if you’re not the museum-type, the walking tour of some of the town’s historic homes could be fun. Top off the weekend with a $5 tour of nearby Red Hook Brewery — even though it’s Seattle-based, Portsmouth is their east coast headquarters.

Even more info here.

The 5 Best East Coast Road Trips for Fallvia

3. Kingston, NY

Why: Another plug for one of my personal favorite spots — our wedding location. Just two hours north of NYC, it’s a good balance between a tucked-away nature escape and a hipster’s hot spot, depending on what you’re looking for.

What To Do: On your way up, make a stop over at either Walkway Across the Hudson {best on warmer / less breezy days} or Beacon, New York. We almost got married in Beacon and I adore all the shopping, restaurants and small town feel. It could be a trip on it’s own! Meander through the hippy town of New Paltz, take a hike through Mohonk Mountain Preserve or splurge on a spa treatment at the Mohonk Mountain House. If the weather is warm enough, have dinner on the back patio at Boitson’s, followed by cocktails at Stockade Tavern — you’ll swear both places were plucked straight out of Brooklyn. Sunday calls for a farmer’s market or apple picking!

Even more info here.


4. Burlington, VT

Why: Close friends of ours had their wedding here a few years ago. It was June and the weather couldn’t have been more perfect. But it really would be the perfect destination for leaf peeping. I can just imagine some of these trees in full-fledged color changing season, right?

What To Do: The drive from Boston or New York weaves through sprawling countryside, which would be beautiful in its own right. Start at the Burlington Farmer’s Market, which runs until the end of October. Take a drive to Shelburne Farms, explore the miles of walking trails and stunning views of Lake Champlain and the Adirondacks on the New York side of the lake. Enjoy a drink and/or dinner in the industrial, waterfront restaurant, Waterworks. Take a tour of locally-started brands, Ben & Jerry’s ice cream {$4 tour} and Magic Hat brewery {free}.

Even more info here.
Dining recommendations {since we were mostly fed by the wedding party} here.

The 5 Best East Coast Road Trips for Fallvia

5. Rochester, NY

Why: You may remember that we visited my sister in Rochester last fall and had such a great time, that another visit was in order this fall. I was pleasantly surprised on our first visit to see why my sister loves it so much. This year, I expected it to be eclectic and interesting and was really happy to be back. It’s worth the 5-hour drive, promise!

What To Do: Grab a donut at Boxcar on the way to the Public Market {Saturdays only}. If it’s still nice out, hike Chimney Bluffs; I’m obsessed! If not, visit the Conservatory or the George Eastman House, browse the shops in the South Wedge, making sure to stop by Abode. Go bowling at Radio Social or have a local beer on the roof at Genesee. Make reservations at Good Luck for high-end family style or head downtown to Branca {get the squid ink pasta and a pizza}. Have a fancy cocktail at The Daily Refresher before bed. On Sunday, go apple picking & grab apple cider donuts at Schutt’s.

Even more info here.


In addition to all of these cities we’ve already visited and would definitely go back to, I also have The Berkshires, The Finger Lakes, Long Island’s North Fork, and Cooperstown, NY on my list to visit. If you have a favorite east coast road trip destination, I’d love to hear about it!

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  • Reply
    Katie Kubtiz
    October 19, 2017 at 5:20 pm

    I’m headed to Burlington next month!! Can’t wait to hopefully see some foliage, if I don’t miss it, and to take some quick road trips. Thanks for pointing me to food and day trip options!

    xx Katie

    • Reply
      Jess at Bubbly Design Co.
      October 19, 2017 at 6:40 pm

      That’s so exciting! I love Vermont 🙂 have a great trip and can’t wait to hear what you do/eat/see!

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