13 Best Small Towns I Visited in 2019

I love small towns and wanted to share the best small towns from 2019! The pace is slower, the people are friendlier, and there’s always something to write about. Some small towns on my list are places I’ve been to before but got to know better; the others are new to me.

Grand Junction

Starting in February, I visited my parents in Grand Junction, Colorado. Ever since they moved into a nursing home, I’ve had to find a place to stay when I visit. I’ve stayed at AirB&B properties exclusively in 2019 when visiting Grand Junction-GJ as the locals call it. By staying with homeowners, I’ve got to know GJ better through their eyes.

The first Airbnb stay was with Abram, a young man who bought an old Victorian home near downtown GJ. Abram and I share of love of rock climbing, and I enjoyed talking with him about his climbing and knowledge of the area. Through Abram’s advice on where to eat, I started going to Bin 707 Foodbar where the food is terrific and the staff friendly.

West Virginia

The next best small town visit was Berkeley Springs, West Virginia. I was invited to the International Water Tasting Competition and found a town proud of their hot springs and water quality. Walking the streets of Berkely Springs and taking in all the history of hot springs culture was big fun.

The best meal was at Lot 12 Public House. Dinner was so good; I’d go back just to eat there. My wife and I both enjoyed the bathhouses and massages at Berkeley Springs. Even though the town is in West Virginia, it was an easy drive from Baltimore.

Makawao

My wife and I went to Maui for a seven-day escape from the Mid-Atlantic winter and loved the small town of Makawao in the Up Country. We met several interesting folks at the local craft’s market and had a delicious meal at Hibibi On Maui, a small outdoor restaurant serving Mediterranean fare.

We drove to the top of Haleakala Volcano, swam with sea turtles, went sea kayaking, visited the aquarium, and generally had a blast. Our stay at What a Wonderful Life B&B was fabulous, and our hostess was able to guide us to Kamaole Beach, where we saw sea turtles close-in and breaching humpback whales offshore.

Cape Charles

Over the last four years, I’ve been exploring the Delmarva Peninsula and finding fantastic places to visit. In May, I went way south on the Delmarva to Cape Charles, VA. This old railroad town is experiencing a renaissance long after the last train left the station.

A mix of pedestrians, golf carts, and cars fill the streets during summer. Cape Charles has a beautiful town beach with lots of sun, ospreys hunting for food, a plus safe swimming, and wading. Several great restaurants and bakeries feed the hungry visitors and locals, while a cidery and brewery quench their thirst.

Cape Charles may be one of the best small towns on the Delmarva Peninsula. Though mostly a summer destination, don’t miss spring and fall in this burb by the Bay.

Franschhoek, South Africa

Honestly, I never had a desire to visit Africa, but when my wife and sister signed up for a safari, I paid more attention to stories in magazines and websites.

It took a year from the time they committed to going on safari until the actual flight to Johannesburg in May. During that long stretch, I became enamored with Cape Town and the wine country. When a bargain fare showed up, I pounced on the flight from Baltimore to Johannesburg and added a short hop to Cape Town.

My wife and sister joined me three days after I arrived in Cape Town, post-safari, and we rented a car to get us to Franschhoek. Our Airbnb was fabulous! A cute over-the-garage unit provided us with great views, and it was walking distance to town.

Mountains, vineyards, and blue skies surround Franschhoek, making it a postcard-like setting. I loved Rickety Bridge Winery and brought back several bottles of their pinotage. At La Petite Colombe, we had one of the best meals of the year with their “winter tasting menu” paired with wine. I’d happily return to South Africa’s wine country if airfare bargains warrant the trip.

Fairhope, Alabama

In June, most of my family and spouses went to Fairhope, Alabama, for my aunt’s 100th birthday party. I had been to Fairhope several times, but this time we rented a large and luxurious Airbnb house in the center of town. With only a short walk to everything in downtown Fairhope, we got to know the town way better.

Yes, they have a great bookstore (Paige & Pallet), but we also enjoyed excellent dining at R bistro, Tamara’s, Another Broken Egg -(a chain restaurant), and wine at Alley Bistro. My wife and I loved the visit so much; we returned in December to visit aunty and explore the town even more. We discovered possibly our new favorite wine bar, Red or White Wine Bar.

Rock Hall, Maryland

My favorite magazine, Edible Delmarva, assigned me a story on Rock hall and Oxford, two historic Chesapeake Bay towns. Both of these towns are tiny, with less than 2,000 year-round residents. And both places filled me with enough ideas for several stories to write soon.

Rock Hall has held on to its roots as a watermen’s town while attracting tourists too. A sailing trip out of Rock Hall, followed by a feast at Pearl on Main, followed by live music at Mainstay, is hard to beat.

Rock Hall has several murals worth tracking down. With scenes of marine life and watermen, the murals capture the essence of this place on the shores of the Chesapeake Bay.

Oxford, Maryland

In Oxford, I took a ride on America’s oldest privately-run ferry, stayed at America’s oldest Inn, and ate some of the best ice cream ever. Walking the town is fun and easy, whether you are going out to eat, or just enjoying some light exercise.

My dog Sophie and I loved walking the town and catching glimpses of bunnies in several places. Restaurants like Capsize are dog-friendly for alfresco dining. Oxford is one now of my favorite small towns.

Round Pond, Maine

My wife’s parents joined us for a trip to a part of Maine we’d never seen. We procured an Airbnb house for our stay in a tiny corner of Maine’s coastal region. We didn’t know what to expect of our trip to Round Pond, as the internet stories and photos were scarce.

As we pulled in to the driveway of our rental home, the old farmhouse stood proud and tall in a clearing in the Maine woods.

We spent our three-day stay getting to know the village of Round Pond and the lobsterman vibe of the area. Old Victorian homes still grace the town, looking much like it did 100 years ago. We ate our fill of lobster from the local co-op, got a pie from Dot’s Bakery, a breakfast/bakery restaurant, and lived it up in style.

Damariscotta, Maine

When we were close to Round Pond, we passed through Damariscotta and noted the old drug store and other shops to come back and investigate. During our stay at Round Pond, we spent several hours checking out the shops of Damariscotta, their farmer’s market, and the Lobster Haul restaurant.

The Lobster Haul is the real deal! This family-run business was started by a lobsterman who wanted his own restaurant to sell his lobsters. We had steamed lobsters, lobsters rolls, lobster mac n’ cheese, and salad outdoors on their patio.

Easton, Maryland

Once again, an assignment from Edible Delmarva Magazine took me to the Eastern Shore. This time it was to write about Piazza Italian market. From that visit, I fell in love with the town and secured a future comped stay at the Hummingbird Inn.

I returned the next month with my dog Sophie in tow for our dog-friendly B&B stay at Hummingbird Inn. Even though it was hot – in the low 90s, Sophie and I had a blast exploring the town. Eric was a perfect B&B host and I can see why his Inn has excellent reviews on Tripadvisor.com, especially for breakfast.

Easton and the well-preserved downtown impressed me, and I returned with my wife for a stay at the Tidewater House, a luxurious mansion with five fabulous suites. The on-site manager, Abigail, is from Colorado, and we had lots to talk about during that stay.

With so many great restaurants to dine at and places to stay, Easton is one of the best small towns in Maryland.

Lewes, Delaware

In October, I was invited to take a ride on the Lewes-Cape May Ferry. I had been to Lewes briefly in 2018 but found out I didn’t know squat about this historic town on the shores of Delaware Bay. I had dinner at Heirloom, one of the best meals of the whole year, then caught the ferry to Cape May for the night.

Sophie loved her first ferry ride, even though at night, it was a boring ride. The next day we came back to Lewes by ferry, and there were about 100 passengers on that ride. We rode up top in the open air, where Sophie was lavished with attention by many of the passengers, making the 90-minute crossing fly by.

Back in Lewes, I went to the Zwaanendael Museum and learned much about the maritime history of the region, including the numerous shipwrecks offshore. The Rodney Hotel looked interesting enough for me to go in and request a tour. This 1920s classic is homey and will be on my radar of places to stay in the future.

Cape May, NJ

I had been curious about Cape May since my time in the Coast Guard. Many of my shipmates had gone to boot camp there and told me about the historic seaside town. The Boarding House Hotel invited Sophie and me to enjoy a nod to the surfing culture of the area.

Sophie found the hotel to her liking as there was a useful grassy area just across the street for sniffing and other duties. I liked the clean and quiet room, plus the surfing board theme.

On the morning after arriving, we hit the road to drive the streets of Cape May and take a walk on the beach. Sophie loved the feeling of sand between her toes, and I enjoyed the salt air and exercise. The Cape May Lighthouse was on my radar of places to visit, little knowing one of the most visited birding sites in the US was next to the lighthouse.

We walked over to the Cape May State Park’s viewing platform and beheld many varieties of waterfowl and even a few raptors. Birders were hefting large cameras and shooting photos of the abundant avian life all around us.

We caught the 1 p.m. ferry departure and enjoyed a warm fall day as we motored across the Delaware Bay. If you go, be sure and ride the ferry a taste of seagoing travel reminiscent of days past when families headed to beach vacations in Mid-Atlantic towns like Cape May and Lewes.

Summary

 The above list of small towns will inspire places to go and unplug for a while. These destinations offer a more relaxing way to enjoy precious vacation time and connect with family and friends. Most of the small towns on the list have opportunities for hiking, biking, or kayaking to get outdoors and get some exercise. See why they made my list and find a few things I might have missed.

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