Stretch Your Legs, Stretch Your Dollars

Each itinerary mixes free or nearly-free ways to move through the county with some things worth spending on.

📅 Before you go: A few stops on these itineraries run limited or appointment-based hours (Teackle Mansion, Ward Brothers Workshop, the Skipjack Heritage Museum). Check visitsomerset.com before your trip to confirm hours and see what else is happening while you’re here.

🎒 Pack for the marsh: Bug repellent, sunscreen, a hat, sunglasses, and a sense of adventure — Somerset’s marshland means mosquitoes and other biting bugs, so come prepared.

1. Waterman’s Weekend

For travelers who want the water, the island, and the working-boat heritage.

Day 1

Morning: Drive the Chesapeake Country All American Road into Crisfield — no admission, no meter.

Mid-Morning: J. Millard Tawes Museum — free, donations requested, covers Somerset’s watermen history and folklife.

Midday: Board the Smith Island Cruises ferry from Crisfield at 12:30 PM — round trip is $35 for adults (12+) and $18 for children (3–11), free under 2; plus lunch on the island at an additional cost.

Afternoon: Explore the island until the 4:00 PM return departure — the Smith Island Center is free to visit, with donations requested.

Optional: Book a tour with Smith Island Eco Tours operator Mark Kitching, an NAI certified interpreter, for an islander’s perspective — additional cost, and arrangements need to be made before you go.

Evening: Dinner back in Crisfield — the island has no restaurant open for dinner, so plan to eat after you return. (Staying overnight on the island means bringing your own groceries — there’s no dinner service there.)

Day 2

Morning: Paddle the Janes Island State Park water trails — self-guided, minimal launch fee. Bring your own kayak, or rent one from the Camp Store; if they’re out, Crisfield Kayak and Canoe also offers in-park rentals.

Midday: Drive from Janes Island to Crisfield and park near City Dock, then walk the Crisfield Arts & Entertainment District from there. Prefer two wheels? Janes Island also rents bikes — ask the Camp Store about the safest route into Crisfield before you set out.

Midday: Drive or cycle out to Ward Brothers Workshop in the “Down Neck” area, a few miles from the Tawes Museum, to see decoy-carving heritage — it’s too far to walk. Open every other Saturday in season and by appointment; call the Tawes Museum for dates, times, or to arrange a visit.

Evening: Sunset at Wellington Beach — no entrance fee.

What it costs

Your ferry fare, meals, and whatever you choose to donate at the Tawes Museum and Smith Island Center. Everything else is free. Lodging: a waterfront rental or inn suits this trip’s pace — expect mid-range to premium rates for water views.

⛵ Prefer a guided day trip over the self-guided ferry crossing? Experience Smith Island also offers a single-day version departing Crisfield at 10:30 AM and returning around 4 PM — $255 per adult and $204 per child (12 and under), for groups up to 6. It includes stops at all three island villages, a crabbing demonstration, a Smith Island cake baking demonstration, entry to the Smith Island Center, and lunch. This is a swap for the itinerary’s ferry-plus-lunch-on-your-own approach above, not an add-on — contact Experience Smith Island directly to book.

🏝 Want the full island experience? This itinerary is a day trip, but Experience Smith Island also runs an all-inclusive 3-day, 2-night package departing from 715 Broadway in Crisfield. Explore all things Smith Island and enjoy a Day 3 day excursion to Tangier Island, VA before heading back to Crisfield. Cost is $1,500/adult and includes transportation from Crisfield, accommodations, and all meals. Guides Capt. Everett Landon and his wife, Carole Ann, are both NPS certified Chesapeake Storytellers. It’s a separate, longer trip from the itinerary above — contact them directly for full package pricing and availability.

2. Back Roads & Byways

For travelers who’d rather drive slow and stop often than check off a list.

Day 1

Morning: Start in historic downtown Princess Anne — free to walk, browse, and photograph. Pick up the walking tour brochure to guide your route past the town’s historic homes and buildings. Duck into Somerset Choice Antiques or Somerset Hidden Treasures — prices are reasonable for a genuinely memorable souvenir. Peek into the Boxwood Gardens at Washington Street and Somerset Avenue, a small, privately owned garden — if the gate’s open, you’re welcome to explore. If UMES is in session, the Mosely Gallery is open during regular business hours (and exhibit opening nights) with a wide, eclectic mix of student and faculty work plus traveling art exhibitions.

Midday: Teackle Mansion — free admission, but only open Saturdays and Sundays, 1 to 3 PM, so time this one carefully.

Early Afternoon: Drive the Chesapeake Country All American Road toward Deal Island.

Afternoon: Visit the Skipjack Heritage Museum in Deal Island — open Saturdays and Sundays, and by appointment.

Evening: Stay in town for dinner in Princess Anne, or make the drive out to Rumbley for dinner and a sunset at the Goose Creek Pit-n-Pub — Deal Island itself has no restaurants, so plan to eat before or after your visit there.

Day 2

Morning: Somerset Trail Mix — hike, bike, or walk a stretch, free of charge.

Midday: Continue on the Chesapeake Country All American Road to its terminus in Crisfield.

Afternoon: Tawes Museum (free, donations requested) and the Arts & Entertainment District galleries.

Evening: Sunset walk on Terrapin Run Trail — free, open daily, no permit needed.

What it costs

One meal out, one museum stop, maybe a small antique find. Lodging: base yourself in Princess Anne — it’s centrally located for everything on this trip. Deal Island has a few short-term rentals but no hotels, motels, B&Bs, or restaurants, so Princess Anne is the practical hub.

3. Free & Easy Weekend

For families and budget-first travelers — built almost entirely on no-cost stops.

Day 1

Morning: Raccoon Beach and Park in Westover — free admission, it’s a county park. Worth a stop, though it’s not large enough to bill as a proper walk.

Midday: Picnic and swim at Wellington Beach — no entrance fee.

Afternoon: Take one of the many Somerset Trail Mix loops — hiking, cycling, or walking, free of charge.

Evening: Terrapin Run Trail at golden hour — free.

Day 2

Morning: Janes Island paddle trails — self-guided, minimal launch fee. Bring your own kayak, or rent one from the Camp Store; if they’re out, Crisfield Kayak and Canoe also offers in-park rentals.

Midday: Paddle the yellow water trail to its landing spot, then walk over the dune to a sandy Tangier Sound shoreline for a picnic lunch.

Afternoon: Once you are back from your water trail adventure make your way to the Crisfield waterfront; ice cream stop optional.

Evening: Dinner at one of the local restaurants and the sunset at a county park or beach of choice.

What it costs

One paddle-trail launch fee and whatever you choose to eat. Everything else is free. Lodging: this is the trip to camp — Janes Island State Park campsites keep the whole weekend budget-first.