The Elegant Eastern Shore Escape, Oxford, Maryland

During our boating journey around the US, we visited the secluded Oxford, MD, and were shocked at how peaceful and artsy the town was. We didn’t have much time to research Oxford before visiting, but when we stumbled upon some of the best home-made ice cream in the United States, cute hand-painted picket fences all around town, and the elegance of a picturesque American town, we knew we would be back.

Oxford, MD Travel Summary

Read below for all the details and everything related to Oxford, MD. Otherwise, here’s our too-long didn’t read giving you what you’ll find in this article at a glance:

• 🇺🇸 Oxford is the postcard picture of America; you’ll come for America’s History and stay for the charm.
• 🍦 Don’t miss one of the best homemade Ice Creameries in the Country – Scottish Highlands Creamery.
• 🍝 Taste the homemade pasta and sauces at Pope’s Tavern.
• ⛵️ Enjoy the rich maritime history either by traveling on the oldest private ferry, kayaking the harbor, or watching the local regattas.
• 🕰️ Check out the oldest full-service Inn in the Country, Robert Morris Inn named after “The Financier of the Revolution”.
• 👀 Spot the local artists’ white picket fence artwork throughout the town.

Check out our other articles in Maryland.

A Brief History of Oxford MD

Once the largest port of call in Maryland, Oxford’s rich history dates back to the late 1600s. It quickly became a trading post for tobacco until the American Revolution, when its cash crop changed to wheat. Oxford’s history is based on the water, like Solomons Island or other Bay towns we’ve written about. Oxford became a world-class shipbuilding town, but, as you’ll read below it’s still commited to its local watermen, the individuals who head out every day for their livelihood.

Why you should visit Oxford, Maryland

We’ve heard of Oxford being described as the ideal postcard of America, and taking a stroll down their main street exemplifies this; with the beautifully manicured lawns, white picket fences surrounding hundreds of year-old homes, and a small town culture, you could imagine yourself growing old here. There was something undeniable about Oxford, MD: tranquillity.

Whether you make a trip to Oxford specifically or just an Eastern Shore road trip stop, visiting Oxford will fill your cup with its outward beauty and what’s hidden underneath. It’s the small things that make Oxford stand out to us. The large community garden next to the even larger dog park shows their focus on the community. The large waterfront docks and parking reserved for local watermen instead of tourism show their focus on the individuals working out in the Bay daily. Finally, while they may have a few restaurants, the ones they have are lauded for their quality and originality. Oxford is a small town, and shows what small towns strive for in America.

How to get to Oxford

Oxford is on the Eastern shore of Maryland in a region known as Delmarva (Delaware-Maryland-Virginia). You access Delmarva from the North, which leads to Philadelphia, from the West over the Bay Bridge near Annapolis, or from the South via the Bay Bridge Tunnel. Most people will take the Bay Bridge, after flying into Washington, DC. Keep in mind that the Bay Bridge and Bay Bridge Tunnels are both toll routes, although they come with some incredible views!

Where to stay in Oxford

Oxford has several unique places to stay, mainly in old inns that have been around for hundreds of years. Don’t expect a luxury stay, but instead enjoy staying in an establishment that may have been visited by our forefathers.

Robert Morris Inn

Robert Morris Inn is the oldest full-service Inn in America. Its origins date back to the late 1600s, and it is located at the tip of the Oxford Peninsula. Robert Morris was known as the “Financier of the Revolution,” and his signature is on many of our founding documents. It’s widely believed that without his financial guidance, we would not have had the funds to win the American Revolution.

The Oxford Inn

The Oxford Inn is in the center of town, right across the street from their local park, Causeway Park! It is an old inn, just like the Robert Morris Inn, although much more recent. Circa 1880, it’s a couple hundred years newer than the Robert Morris Inn (it reinforces just how old the Robert Morris Inn is!). The Oxford Inn is a great home base for your time in Oxford because it’s also the location of one of the best restaurants in town, Pope’s Tavern!

Sandaway Suites & Beach

Sandaway Suites & Beach is even newer than the Oxford Inn and near Robert Morris Inn, near the peninsula’s tip. This Bed & Breakfast has positioned itself as the adults-only retreat to Oxford. You have a private beach overlooking the Tred Avon River and the Chesapeake Bay. If you time your trip right and visit in August, you may even have prime location to view the sailing regattas on the water! Regardless, you will get some beautiful sunsets.

Our Oxford Restaurant Recommendations

Oxford exemplifies the saying, “quality not quantity”. There may not be many to choose from, but here are our recommendations!

Scottish Highland Creamery

This was our favorite place to eat while we visited Oxford! Scottish Highland Creamery just upgraded to a building near the museum in the central part of town, but we went to their original location… a hole in the wall right next to Capsize OXMD! Not only is their handmade ice cream delectable, but they have dog ice cream, too. I think Ollie echoes our love for Scottish Highland Creamery.

You’ll most likely notice the ice cream shop from far away, as a line of people will be out the door. I remember thinking, “Where are these people from?” because Oxford seemed so small! Scottish Highland Creamery was rated one of the country’s top 5 ice cream shops, and they didn’t disappoint!

Pope’s Tavern at the Oxford Inn

Pope’s Tavern is only open for dinner six days a week, and if you want breakfast, you’ll have to stay at the Inn. Pope’s Tavern is a little slice of Italian heaven with homemade pasta and sauces made from local ingredients! A great date night, you should try the Rigatoni Vodka and their Ricotta Cheesecake for dessert.

Docs Sunset Grille

At the other end of the restaurant spectrum from Pope’s Tavern, Docs Sunset Grille is a local spot to grab a drink. You can watch the dreamy Chesapeake Bay Sunsets, eat local crabs, and try the Maryland state drink, an Orange Crush!

Capsize OXMD

Capsize OXMD is in a prime spot, right next to the Oxford town dock (and right next to Scottish Highland Creamery). They are only open in the tourist season, so make sure you check the dates if you’re visiting Oxford in the Winter. Capsize is dog-friendly, and an excellent way to think of it is between Pope’s Tavern and Docs Sunset Grille. Not quite as fancy as Popes but not as chill as Docs. You can even stay overnight for a small fee and make your boating outing an overnight adventure!

Anthony’s

Anthony’s is the new restaurant that took over from Latitude 38 (who sold their restaurant in 2022). As an Italian New York chef-curated fine Italian restaurant, Anthony’s is another great spot for your date night in Oxford!

What to Do in Oxford, MD

There are many different ways to see the elegant Oxford, MD, depending on what you’re looking for. Here are our three recommendations:

Act like a local

Pretending to be locals is Jen and I’s favorite way to travel. We like to see what the locals do and explore it for ourselves. We recommend going to Oxford Social, the local coffee joint only open Thursday – Sunday Mornings, before walking to the park and wandering through the community gardens on the way to the dog park. Ollie loved being able to run around!

After the dog park, walk back through the main town road and check out all the painted picket fences. Painted by local artists, they sold at the end of the season every year to raise money for charity. See how many you can spot as you wander through town!

Next, head to Scottish Highland Creamery for an Ice cream snack and grab a table to relax and watch boats come in and out of the harbor.

Make a reservation at Pope’s Tavern for some fine Italian Food at 5 pm and then afterward catch the Sunset at the Town Beach or Docs Sunset Grille!

Hit the Tourist Spots

As a tourist, there is a few activities that you wouldn’t want to miss on your visit to Oxford.

The oldest private ferry in the US is located in Oxford, the Oxford-Bellevue Ferry. It started in 1683 with just a scow. Over the years, it’s been upgraded and changed hands many times, but it still operates today! You can get a return trip and enjoy the ride across the Tred Avon River.

The Oxford Museum should be on your list to help you understand Oxford’s rich history. With over 300 years of history dating back to the 1600s, the Museum has cataloged the past since it opened in 1964. With many of the donations from local families, you can get the authentic history of Oxford.

Finally, you should check out the Robert Morris Inn and grab a bite to explore their local grounds in the oldest full-service Inn in the country.

Day Trips from Oxford

Oxford is also a fantastic spot to visit other historic areas on the Eastern Shore. Here are the towns and the distances:

• St. Michaels, Maryland – 30 minute drive
• Easton, Maryland – 16 minute drive
• Cambridge, Maryland – 13 minute drive

Also, if you are interested in St. Michaels, there is a bike trail! It’s 30 miles long, and you can even take the ferry over to make a loop!

Best time of Year to Visit Oxford

Oxford is best visited in Spring and Summer. Outside of April through November, most places are either closed or have reduced hours. Also, week to week you’ll want to visit Thursday through Sunday. Here are some of the holidays in Oxford:

• Oxford Day – Late April
• Oxford Fine Arts Festival – May (2024 is this festival’s 40th year)
• Christmas on the Creek – Beginning of Winter

Oxford Average Temperatures

Boaters Guide to Oxford

When we visited Oxford, we did it aboard our floating home, Pivot. We traveled across the Chesapeake Bay from Solomons, Maryland. Here’s everything we learned about boating to Oxford!

How to Approach Oxford

Oxford is just off the Tred Avon River, which connects to the Chesapeake Bay. There is plenty of depth entering Town Creek and to the center, although you’ll want to make sure you check your sonar charts before poking your bow into any of the bays off Town Creek.

Where to Dock in Oxford

There are tons of marinas in the Town Harbor, however, most of these marinas are private boat-building docks, yacht clubs, etc. You can always contact them, and if you’re a Looper, mention that, and perhaps they can open up a spot with a good rate.

Here are some options to get you started:

1. Safe Harbor Oxford: At $3.50 / foot, this is a pricey option but it does come with a swimming pool and the quality that you expect in a Safe Harbor.
2. Tred Avon Yacht Club: This private yacht club has been known to offer its mooring balls ($25 / night) to reciprocating yacht clubs.

Use our Referral Code 450ZMS3 for a $15 discount on your Dockwa reservation!

Where to Anchor in Oxford

When we visited Oxford, we anchored smack dab in the center of Town Creek. It was super protected and right next to a dinghy dock, perfect! However, there is just room for one or two boats here, so our backup option was further back into the Town Creek East Cove.

Here, you’re a bit more exposed, but you still have some protection. You are close to the other main town dock at Capsize OXMD, so it is still good for that. The added benefit is that there is tons of room, so plenty of boats can visit!

For more insights on anchoring, reviews from fellow boaters, and general info about navigating around Oxford, check out Waterway Guide.

Check out our Great Loop Anchorages and Free Docks Spreadsheet with 600+ anchorages!

Internet in Oxford

Internet on the Eastern Shore is very hit or miss. We recommend starlink although you should have a good cell signal! In town, here are a few places you might be able to work from, just ask before setting up:

• Oxford Social Cafe
• Oxford Library

Check out our blog post on Boat Internet!

Provisioning in Oxford

The Oxford Market (the only shop in town) is a small store for provisioning in Oxford. Don’t expect much more than the essentials, but if you’re looking for some small things then you may find them!

Download the free Waterway Guide App to locate marinas, services, anchorages, free docks, navigation alerts, bridges, locks, and more!

Watch our Trip to Oxford on YouTube!