Things to do in Cambridge Maryland: A Fun 3-Day Guide

Things to Do in Cambridge Maryland - visit the lighthouse

If you are looking for things to do in Cambridge Maryland, you’ve come to the right place!

My family discovered Cambridge in the middle of 2020 and now it’s one of our favorite places to visit! We just returned from a trip a few weeks ago and booked a return visit for next year.

I will share some of our favorite restaurants, where we stay, what to do at our resort, and things to do in Cambridge Maryland and St. Michaels – which is only a short ride away.

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Article Contents

Where to Stay in Cambridge Maryland

If you are looking for things to do in Cambridge Maryland, chances are – you are already booked at the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina.

I’m sure there are other hotels and AirBNBs in the area, but this resort is our favorite for so many reasons.

The rooms are spacious – which is ideal when staying with two kids. In the past, we’ve stayed in a standard two-queen room and found it perfect for comfortably sleeping all four of us.

For our most recent trip, we decided to try out the King family suite – which has a king-size bed and bunk beds – purely for the novelty of the bunk beds. The kids were delighted with bunks and we appreciated that it freed up space for a seating area between our bed and theirs.

The resort in Cambridge MD is situated right on the Chesapeake Bay and has gorgeous views, along with walking trails right along the bay. With plenty of benches and rocking chairs, you can easily wily away the day by relaxing and watching the water.

Things to Do at the Hyatt Regency Chesapeake Bay Resort

There is so much to keep your family occupied at the Hyatt Chesapeake Bay – you genuinely don’t ever have to leave the resort if you don’t want to.

Let’s start with the pools – there are 3. An adult-only infinity pool, an activities pool with a waterslide, and an indoor pool to enjoy all year long. The indoor pool is home to the nightly movie – which plays as it gets dark, so your kids can swim and enjoy a flick at the same time!

Additionally, you’ll find the following activities on-site for free:

Mini Golf
Beach Volleyball
Tennis
Basketball
Gym
Hiking Trails
Giant Chess
Frisbee Golf
Horse Shoes
Cornhole
Outdoor Fires (s’mores cost extra)

There is also an arcade, golf, private firepits, and a spa – but those are all additional expenses.

In season, from Labor Day to Memorial Day, there are additional activities available to rent on-site from Blackwater Adventures including bicycles, jet-skis, kayaks, paddle boats, stand-up paddle boards, and other boat rentals. You can also sign-up for guided tours!

When we went over Memorial Day, they also had hourly kids’ activities, bounce houses, games, and other fun things available at no additional cost.

Where to Eat: Cambridge MD Restaurants

There are restaurants on-site at the Hyatt, but we found the local fare to be much better. We generally eat lunch at the resort by the pool or from the marketplace (which also has sandwiches, coffee, snacks, and breakfast options) or skip it if we had a big brunch.

If you wanted to skip lunch at the resort, many of the breakfast and dinner restaurants below would also work for lunch.

Now let’s get into some of our favorite Cambridge, MD Restaurants.

Breakfast Restaurants in Cambridge MD

If you can only eat at one breakfast spot, make it Blackwater Bakery. Their breakfast meals are delicious and their baked goods are to-die-for! We always try to eat here on our last morning so we can load up on bakery items for the ride home. Of all the Cambridge MD restaurants, this is my favorite.

My husband is mad about the crab omelet, my kids love the avocado toast and acai bowl, and I’m crazy about the quiche. Their honey lavender chai is incredible – I’ve been looking for something similar at home, but nothing I find is as good as theirs.

For more of a grab-and-go meal, head to Bay Country Bakery for homemade donuts and coffee cake that will satisfy any sweet tooth. We didn’t have a chance to try their breakfast sandwiches – but we got to see (and smell) them being made. I’ll be adding one to my order next time.

Take a photo of the giant donut painted on the walls of the bakery while you are there – it’s the perfect backdrop for a fun family picture.

For simple diner food that is authentic and delicious, we also really like Cambridge Diner. The portions are enormous and taste exactly like you want a diner breakfast to taste – homestyle and delicious!

Dinner Restaurants in Cambridge MD

When we first started going to the area, the restaurants in Cambridge MD meals weren’t as plentiful, but now there are tons of yummy spots popping up around town!

Let’s start with Snapper’s Waterfront Cafe and Tiki Bar. We’ve been to other spots on the water for dinner in Cambridge, but Snapper’s blows them all out of the water. Their broiled crabcakes are made with crab shucked at the factory next store and the jerk chicken tastes like it’s from Jamaica.

Ava’s Pizza was originally from St. Michaels, but they just opened up a location in Cambridge, MD that’s just as good. The meatballs melt in your mouth, the Caesar was delightful, and then there’s the pizza!!! We tried the Mediterranean Pie, a Meatball Breeze, the Chef’s Favorite, and a monthly special. Each was better than the next!

High Spot, owned by Ava’s, is new to Cambridge as well. It’s located in the heart of Downtown Cambridge and features American-style food with an upscale twist. From fried pickles to burgers, crabcakes to fried chicken, this restaurant will please even the pickiest eaters.

Things to Do in Cambridge Maryland

Cambridge, Maryland is set in gorgeous Dorchester County and is situated right on the Chesapeake Bay. It’s close to nearby St. Michaels, and not far from Annapolis either. There are so many things to do in Cambridge Maryland, and the surrounding areas, so I put together a guide for an ideal first visit.

3-Day Itinerary w/ Cambridge Maryland Restaurants

Day 1 – Arrival

Check into the Hyatt Chesapeake Bay, explore the resort to get your bearings, and play a round of mini golf before dinner.
Grab some crabcakes at Snapper’s Waterfront Cafe and Tiki Bar for dinner
Stay for live music or head back to the resort for a nightcap.

Day 2 – Explore Cambridge

Head to Bay Country Bakery for donuts and cinnamon buns.
Spend the day at the pool, play some frisbee golf, and talk a walk around the docks
Grab lunch at the poolside cafe located near the indoor pool
Sail on the Skipjack Nathan in season or head to Blackwater National Wildlife Refuge for a kayaking adventure all year.
Snack on a burger at High Spot
Catch a movie at the indoor pool

Day 3 – Visit St. Michaels

Wake up and grab a coffee at the marketplace before driving the 40 minutes to St. Michaels
Sip mimosas during brunch at The Galley – voted the best brunch on the Chesapeake
Visit the Chesapeake Bay Maritime Museum to explore a lighthouse, learn about boatmaking, and find out the role St. Michael’s played during the war.
For lunch, go to the St. Michael’s Ava’s Pizza for a slice of prosciutto and mozzarella pizza.
If you didn’t go sailing yet, take a trip on Sail Seline
Otherwise, head down Talbot Street for cute boutiques, ice cream parlors, and home decor stores.
Indulge in the seafood sampler at The Crab Claw
Back at the resort, rent a firepit by the water for S’mores at Sunset

Departure Day

Check out and head to Blackwater Bakery for a crab omelet. Stock up on snacks for the way home.
Drive to the Harriet Tubman Underground Railroad Visitor Center and National Park to learn about Harriet Tubman and her role in the Underground Railroad at this interactive exhibit.
Head home