🌿 Guest Q&A: Everything You Need to Know

Welcome to the Eastern Shore of Maryland!

Q1: Where exactly is the Eastern Shore of Maryland?

A: The Eastern Shore sits on the Delmarva Peninsula — land nestled between the Chesapeake Bay to the west and the Atlantic Ocean to the east. Princess Anne is a charming small town about 2.5 hours from Washington D.C., 2 hours from Baltimore, and 3 hours from Philadelphia. If you've never crossed the Bay Bridge — buckle up, it's a moment.

Q2: Do I need a car?

A: Yes, absolutely. The Eastern Shore is rural and beautiful, but rideshare options (Uber/Lyft) are very limited outside of Ocean City. Rent a car, carpool with fellow guests, or coordinate with your hotel. Getting around independently will make your trip so much more enjoyable — and the scenic drives through farmland and waterways are honestly half the experience.

Q3: Where should I stay?

A: You have wonderful options across several areas, with something for every style and budget. Each location offers traditional hotels, boutique inns, Airbnbs, and Vrbo vacation rentals:

— Salisbury, MD (15 min away) — Most convenient home base. Major chains like Marriott, Hampton Inn, and Hilton Garden Inn, plus local Airbnbs and rental homes throughout the area.

— Ocean City, MD (30–40 min) — Perfect if you want to extend the trip into a beach getaway. Tons of hotel options, countless Airbnbs, and Vrbo condos right on the water.

— Cambridge, MD (45 min north) — Charming waterfront town. The stunning Hyatt Regency Chesapeake Bay is a splurge-worthy resort option, with beautiful Airbnb homes along the water as well.

— Berlin or Snow Hill, MD (20–30 min) — Quaint, walkable small towns with lovely B&Bs, inns, and cozy Vrbo cottage rentals for a tucked-away feel.

Q4: Should I book accommodations early?

A: Please don't wait. The Eastern Shore fills up fast, especially during fall festival season. Book the moment you confirm attendance — options go quickly and prices rise as the date approaches.

Q5: What's the weather like in early October on the Eastern Shore?

A: Early October is honestly one of the best times to visit the Shore. Here's what to typically expect around October 3rd:

— Daytime highs: 65–72°F — comfortable and pleasant

— Evening lows: 48–55°F — noticeably cooler once the sun goes down

— Conditions: Mostly sunny with low humidity; the thick summer air is long gone

— Fall foliage: Just beginning to show, with golden and amber tones starting to appear across the farmland and tree lines

— Wind: Light breezes are common, especially in open clearings

What to pack: A light-to-medium layer for the evening is a must — what starts as a warm afternoon can feel quite cool by sunset. Think a stylish wrap, blazer, or light jacket that complements your outfit. Ladies, a pashmina or cardigan works beautifully. Gentlemen, a sport coat does double duty here.

Q6: We're from the Midwest — how different will this feel from home?

A: You'll actually feel right at home in many ways — the Shore has that same warmth, friendliness, and wide-open landscape that Midwesterners love. What's different is the water is everywhere. Creeks, rivers, the Bay, marshlands — it's a beautifully unique coastal ecosystem. Early October brings crisp, dry air that feels very familiar to a Midwest fall, just with a slight saltwater breeze and the sound of waterfowl overhead.

Q7: Will there be bugs?

A: Good news — by early October, the mosquito situation has improved significantly compared to summer. You may encounter a few in the evening near wooded or marshy areas, but nothing like the summer months. A light bug spray tucked in your bag is smart just in case, but most guests won't need it at all.

Q8: What should I absolutely eat while I'm here?

A: Do not leave the Eastern Shore without experiencing these:

— Maryland Blue Crabs — steamed and seasoned, eaten at a paper-covered table. This is non-negotiable.

— Smith Island Cake — Maryland's official state dessert; a stunning multi-layered confection

— Fresh Chesapeake Oysters — fall is prime oyster season, so your timing is perfect

— Eastern Shore Fried Chicken — a beloved regional tradition

— Rockfish — locally caught and beautifully prepared at most Shore restaurants

Q9: What should I wear to the event?

A: Smart casual and comfortable — think garden party meets backyard cookout. Lean into the event colors: evergreen, gold, white, and tan. Given the October weather, a chic layer for the evening is highly recommended. Skip the stilettos — we're on one acre of gorgeous grass — and leave anything uncomfortably fitted at the hotel. Look lovely, breathe freely, and enjoy yourself.

Q10: Is the venue accessible?

A: The event is held in a one-acre grassy clearing on natural ground — not pavement. If you have mobility considerations, please reach out to us directly so we can ensure you are comfortable and well accommodated.

Q11: What time should I arrive?

A: Please arrive on time or just a few minutes early. Unlike a church or banquet hall, an outdoor gathering on private property has no lobby to wait in — and navigating a grassy clearing late means an audience. We all want to avoid that. You included.

Q12: What if it rains?

A: October on the Shore is generally dry and mild, but we always have a plan. We have a contingency plan in place and will communicate any changes as early as possible. Tucking a compact umbrella or light rain wrap in your bag is always a smart move for any outdoor fall event.

Q13: Any helpful tips for getting around?

A: A few practical notes:

— Download maps offline — cell service can be spotty in rural areas

— Bring some cash — farm stands, local markets, and some beloved crab shacks are cash-friendly

— Give yourself extra time — Shore roads are scenic and rural; GPS occasionally gets creative out here

— Find a Chesapeake Bay sunset — it will stop you in your tracks, guaranteed

We are so grateful you're making the journey to celebrate with us. Welcome to one of the most beautiful and soulful corners of the East Coast.