Southern, MD is where the bay breeze meets small town charm, which makes it ideal for an easy weekend escape. This two day plan blends waterfront walks, fresh seafood, quiet beaches, and history so you can slow down without feeling like you missed the good stuff. Use this guide to map simple moves across Southern and return home feeling reset.
Before you hit the road
If a road trip is part of your plan, give your car a quick once over. For peace of mind, schedule a fast pre-trip check with Nationwide Dent & Wheel Repair so your ride matches the calm you are chasing in Southern, MD.
Day 1 Morning: Coffee, coves, and a lighthouse view
Start in Solomons with a waterside coffee and a stroll along the Riverwalk. Watch boats ease through the Patuxent while you set your pace for Southern, MD. Head to the Calvert Marine Museum to see the Drum Point Lighthouse up close. Exhibits are compact and friendly, which keeps energy high for the rest of your day. If you prefer fresh air over galleries, rent a kayak for a gentle paddle near Back Creek and look for ospreys.
Day 1 Lunch: Crab cakes and a view
Choose a dockside lunch where you can linger. Order a classic crab cake and a simple salad so you can keep moving without a mid afternoon crash. The point is not to rush. Let the water and the chatter around you remind you why Southern, MD feels different from the city. Ask your server for a quick beach tip. Locals are generous with suggestions when you are curious and polite.
Day 1 Afternoon: Cliffs and coves
Drive to Calvert Cliffs State Park for an easy hike. The shaded trail opens to a quiet beach with clay cliffs in the distance. Pack sandals since the last stretch can be damp. This is a favorite spot in Southern, MD because it feels wild yet calm. If hiking is not your thing, try Annmarie Sculpture Garden for a playful loop through art and trees. Both options keep the day light while still delivering a sense of place in the Southern.
Day 1 Evening: Sunset in Solomons
Return to the Riverwalk for golden hour. Grab a bench and watch the light change on the water. For dinner, pick a spot with outdoor seating so you can stretch the evening. Share a basket of oysters and a simple pasta. You will sleep better after an unhurried night, which is the soul of the Southern. If you like live music, check local listings. Many venues book small acoustic sets that fit the mood.
Day 2 Morning: History and a quiet beach
Point the car toward Historic St. Mary’s City. The outdoor exhibits bring early Maryland to life without heavy reading. Costumed guides make it fun and relaxed, and the open fields let you wander at your own pace. Afterward, drive south to Point Lookout State Park. The beach is wide, the water is gentle, and the breeze is steady. This is where Southern, MD feels like a private retreat even on a busy weekend.
Day 2 Lunch: Picnic with a bay backdrop
Pack a picnic with fruit, a bakery loaf, and local cheese. Sit at a shaded table and watch pelicans skim the surface. If you did not plan a picnic, a simple deli stop on the way works fine. The goal is easy choices so you can stay present in Southern, MD. Keep sunscreen and a light shirt handy since the midday sun can reflect off the water.
Day 2 Afternoon: Small town wandering
Head to Leonardtown Square for a slow walk. Pop into a gallery, sample small batch ice cream, and browse a bookstore. Many visitors say this is where Southern, MD charm is most obvious. Shop owners greet you by the door and give tips without a hard sell. If you still have energy, take a short detour to a roadside farm stand for peaches or sweet corn in season.
Day 2 Evening: Last look at the water
Finish with one more waterside meal. Order something simple and fresh so you can focus on the view. Talk about your favorite moments and pick the one you will revisit next time. As night falls, take a final loop along the dock. Let the quiet settle in. This is the memory you will carry home from Southern, MD.
Practical tips that keep the weekend smooth
Travel times are short, yet cell service can dip in pockets. Download a map for backup. Pack sandals for beach entries, a light sweater for breezy nights, and a small cooler for snacks. Parking is usually easy, but keep a little cash for small lots. These tiny details protect your time in Southern, MD so the trip stays simple and sweet.
Plan your next read
Want even more inspiration for your itinerary in Southern, MD? Explore budget friendly ideas and hidden corners in our next guide: 21 Free Things To Do in Southern, MD Right Now.