I’m trying not to count our chickens considering how many times we’ve had to change our road trip plans this year, but we now have the next few months of our road trip planned out.
For a bit of background, COVID-19 has impacted our plans several times over this year, so check out these past posts if you’d like a recap:
- March 12 – Coronavirus: How It Might Affect Our Travel
- March 17 – Coronavirus: How Our Plans Are Changing Drastically
- April 7 – Coronavirus: What It Means For Our Road Trip, Finances & More
- May 5 – These Are Our Road Trip Plans For The Rest Of 2020
- June 17 – Here Are Our New Road Trip Plans For The Rest Of 2020 (Maybe)
- August 26 – Our Plans Are Changing & Changing & Changing Again!
In that most recent post from August 26, I shared all the different plans we’d considered for this fall. One of our earlier considerations was to visit Maryland, but we’d decided against it in the end.
Well, we’re performing a bit of a U-turn because we’re going to be spending most of the rest of the year in Maryland after all, but we have a couple of other places to visit before that. Here’s what we’re up to right now and the cities we’ll be visiting the rest of the year.
Where We Are Right Now
Shae and I just finished up a three week stay just outside of Washington D.C. and drove down to Hampton, VA yesterday. We’re staying here for a couple of weeks so that Shae can visit some of the local museums and attractions for her Traveling Teach classes on Outschool. We used to live in nearby Portsmouth which means we know the area well and so have a good idea of places that’ll be interesting for her to teach about.
Where We’ll Be Going Next
After leaving Hampton, we’ll still be staying in Virginia, but heading west to Roanoke for a couple of weeks. I love Roanoke because it’s in the Blue Ridge Mountains, so it’s a beautiful area with some great hiking, good breweries and restaurants and other fun stuff to do. You can check out our past posts about things to do in Roanoke here.
It’s not really for me that we’re visiting Roanoke though. Instead, it’s for Shae and her mom. There’s a tattoo artist there that they’ve visited a couple of times before, so Shae’s mom will be joining us one weekend so that the two of them can get tattoos together again. I’m not a fan of needles, so I’ll be sitting out that activity!
Shae loves animal experiences, so she has footprint/pawprint tattoos on her foot and lower leg for all the animals encounters she’s had in the past. We’ve had a few more animal encounters since she got those tattoos done, so that’s what she’ll be adding.

We didn’t previously have a firm idea of what to do after Roanoke, but knew we wanted to stay on the east coast and didn’t want to venture too far afield. As a result, Virginia, Delaware, Maryland and North Carolina were all in the running for this fall.
Why We Decided Against Maryland Previously
Back in July and August, I’d been looking into accommodation options in Maryland for September and October, but the hotels and Airbnbs I’d been looking at were all a little more expensive than we’d have liked. They weren’t extortionately priced, but the cash cost would’ve eaten into our budget too much, while using hotel points wouldn’t have been very good value either.
Why We’ll Be Visiting Maryland After All
When doing that original research into hotels in Maryland, the higher-than-wanted prices were in September seeing as that’s when we were originally planning on visiting.
With our subsequent plans changing to include D.C., Hampton and Roanoke, we wouldn’t need hotels in Maryland until late October. That seemed to have a big impact on prices because when doing some new searches, everything was much more reasonably priced. October 1 seemed to be the tipping point, so that must be when the summer tourist season has truly ended.
Being able to find some decent hotel deals means we’ve decided to visit Maryland from late October to mid-December. That works out perfectly because the weather should still be fairly nice, but visiting in off-season means museums and other attractions should be much less busy and therefore make it easier to physically distance while visiting. Although it won’t be quite as beautiful as fall in West Virginia last year, there’ll hopefully still be some nice fall colors while out hiking in Maryland.

Where We’ll Be Staying In Maryland
Frederick
After leaving Roanoke, we’ll be heading to Frederick first. It’s near Hagerstown and has a few places to visit in the area, including Harpers Ferry National Historical Park just across the border in West Virginia. We’d missed out on Harpers Ferry when visiting WV last year, so we wanted to make the effort to drive over there when we were next in the area. The only downside is that it’s not possible to get the full experience right now due to the pandemic.
One of the reasons we chose Frederick is because there’s a good value hotel there which is part of Hilton’s loyalty program. Hilton Honors uses dynamic pricing for award nights which means the number of points required for your stay can be more expensive when the cash price is more expensive. Conversely, the points requirement can go down when the cash price goes down. With October being off-season in Maryland, several Hilton properties cost fewer points per night due to the corresponding lower cash cost.
Hilton also offers every fifth night free on award stays to anyone that has status with them, so we’ve booked a 15 night stay to get three free nights in order to maximize our points further.
The general Baltimore area
After Frederick, our original hope was to stay in downtown Baltimore for a week or two in the Inner Harbor area. Although the hotel prices themselves aren’t too unreasonable considering it’s a city center, parking seems to be about $30 per night no matter which hotel we’d be staying at.

That’s far too expensive, so we’ll probably stay somewhere further out of the city and drive in a couple of times to explore downtown. We’re not entirely sure yet where we’ll stay, but we have a few options. One is to stay at an airport hotel for a few weeks, while another is to stay near Fort Meade as that’s about halfway between Baltimore and Annapolis.
A third option is to stay in Aberdeen. That’s about 30-40 minutes outside of Baltimore to the northeast and has a few interesting place to visit in that general area. The problem with this option is that Annapolis is on the opposite side of Baltimore, so it would be a bit of a drive to visit there. We’ve had a few people recommend Annapolis, so it’s definitely somewhere we want to check out.
Having said that, there’s a hotel in Aberdeen which is great value when redeeming points. It’s an IHG brand and staying for at least a week will help me retain Spire Elite status which is their top-tier status. While IHG’s loyalty program isn’t great when it comes to status benefits, it offers double points on paid stays and 25,000 bonus points when earning the status, so that has me leaning in that direction.
Ocean City
After that, we’ll be spending a month in Ocean City. Hotels in Ocean City can be very expensive during tourist season, but are far cheaper in off-season which begins on October 1. The prices get even cheaper as the year goes on, so being able to stay in a nice oceanfront hotel for less than $75 per night before tax is too good an opportunity to pass up.
We’ll be getting to Ocean City around mid-November, so we’ll be there over Thanksgiving through mid-December. In past years, we’ve sometimes picked up Thanksgiving dinner from Cracker Barrel or Golden Corral. I don’t know if Golden Corral will have reopened by then seeing as buffet restaurants aren’t a great place to visit during a pandemic, so we might need to order from Cracker Barrel. Our portable kitchen means we can sort out some of the side dishes, so it’s mainly the turkey and dessert we’ll need to pick up from somewhere.
What We’ll Do After Maryland
After visiting Maryland, we’ll drive back down to the Hampton Roads area of Virginia. Shae’s dad is getting remarried mid-December, so that’s the main reason we’re heading back. Seeing as that’s just before Christmas, we’ll stick around for another week or two to be near Shae’s family over the rest of the holiday period.
Our New Year’s Eve Plans
With our 50 state road trip taking place over five years, we’d wanted to celebrate New Year’s Eve in five different time zones – Eastern, Central, Mountain, Pacific and Hawaii-Aleutian Standard Time.
In our first year of the road trip (2018) we celebrated New Year’s Eve in Denver, CO, so that was Mountain time zone checked off the list. 2019 was spent in Nashville, TN which is in the Central time zone.
For 2020, we’ll be on the east coast. The problem is, we were saving New Year’s Eve on the east coast for Times Square in New York, but that’s obviously not an option for this year. Even though we’ll be on the east coast as we head into 2021, we’ve decided that New Year’s Eve 2020 doesn’t really count. 2020 has been a bit of a write-off due to COVID-19, so it’s looking like we’ll be having to extend the road trip by a year which means we can hopefully be in Times Square for New Year’s Eve before the road trip is done.
We haven’t decided where to celebrate the ending of 2020, but we’re thinking of Charleston, SC or Savannah, GA seeing as we loved both those cities when we visited them back in 2018.
Final Thoughts
With our road trip significantly slowing down in 2020, it’s nice that we’ll be able to check another state – Maryland – off our list before the year is up, even if the pandemic means we might not be able to get the full experience.
Neither Shae nor I like having a load of uncertainty about our future plans, so it’s nice that we finally have something pretty much decided for the next three months.
BWI airport hotels are, well, airport hotels! There is a Hyatt Place next to a casino if that moves the needle.
Best part is they all have shuttles to BWI where you can pick up the light rail into downtown Baltimore. Good frequency and it’s a couple of dollars each way.
The shuttles will usually drop you at the Amtrak station too for easy access to DC. I know you just did DC but for readers reference.
Annapolis is best midweek as it’s quite the tourist magnet on the weekend.
I’ll be Christmasing at a Hyatt House out west (60 guesses why 😉) with no oven. Is Cracker Barrel turkey good??
Thanks for all those suggestions! I don’t know how I feel about public transport right now, but light rail into downtown Baltimore does sound tempting.
Our month-long stay over Thanksgiving will likely be a Hyatt Place, so that’ll be getting us halfway towards Globalist next year which will be a nice head start 🙂
As for Cracker Barrel turkey, it’s good enough – certainly better than trying to organize something like that in a hotel room, although in theory my Instant Pot could cook a small turkey breast. We’re not a big fan of their Thanksgiving sides though; from what I can remember, the green beans had almonds and the stuffing wasn’t great. We’ll probably do canned green beans and Stove Top stuffing instead of getting those two from Cracker Barrel – we have a small electric kettle, so the stuffing is easy to make.
It might be that some other restaurant is offering Thanksgiving dinners to go, so we might have a look around once we get to Ocean City. I imagine some restaurants close for the season after summer’s over, so it’ll depend on what’s still open.
Look at visiting Fort McHenry and the Walters Museum in Baltimore. The Walters has one of the few Faberge Easter eggs in the US which might be a teaching moment. I would try to get close to the light rail system if you can for travel into Baltimore from your hotel choice.
Wishing I was back in Bali like last year. Nags Head will have to do for a few days next week.
Thanks for those suggestions. It looks like we already had Fort McHenry and Walters Museum on our potential list, so I’ll mark that you’ve recommended them too – it’s always helpful keeping track of places that many people have suggested.
Shae and I were just talking the other day about how we’d love to have been back in Bali right now as we were there last summer. Hope you have a nice time in Nags Head 🙂
While staying Frederick I suggest the National Museum of Civil War Medicine. And, speaking of the Civil War, in addition to Antietam National Battlefield, be sure to visit Monocacy National Battlefield. Both are good sites for short hikes. Regarding hiking Gambrill and Cunningham Falls State Parks and Catoctin Mountain Park (site of Camp David) offer superior hiking opportunities! Enjoy!
Thanks for all your suggestions – I’ve added them to our list 🙂