Best Bachelorette Party Destinations on Maryland’s Eastern Shore

BASHelorette August 16, 2019 No Comments

Best Bachelorette Party Destinations on Maryland’s Eastern Shore

What are the best spots to celebrate a bachelorette party on the Eastern Shore of Maryland? Whether you are a Maryland native or are traveling into town for the bride tribe celebration, there are incredible bach-friendly destinations for groups big and small. One thing is for certain – a bachelorette party on the Eastern Shore of Maryland will be scenic, memorable and fun!

Maryland’s Eastern Shore is known for being quaint, elegant, and, most importantly, full of hidden gems. Bar crawl or B&B’s, Bashelorette has you covered for the perfect weekend getaway.

The Narrows and Kent Island

The first stop across the Chesapeake Bay Bridge lies the humble area of Kent Island. Find a good parking spot and put on your most comfortable (But still stylish!) heels, ladies, this night on the Narrows is about to be unforgettable. Kick off the evening with an early dinner at Bridges Restaurant and award-winning happy hour specials from 4-6:30pm. Named in the 100 Most Scenic Restaurants in America, we promise the view will be almost as good as the food.

Before sunset, make your way to The Big Owl Tiki Bar and enjoy live music while you sip fresh squeezed orange crushes with your gals. If you want a more private setting while still savoring the water-front view, The Big Owl offers their upper deck for up to 50 people, which includes a bar and bartender that are all yours! Reservations can be made via email.

Regardless of what you choose, trust us and end your night at The Jetty. With last call at 1:30am, this island classic offers the best nightlife around. Afterwards, the complimentary bus service back to your hotel. We suggest The Hilton, Holiday Inn, or Best Western.

St. Michaels and Oxford

For a celebration equally as fun, but maybe a bit more extravagant, take the scenic route down to St. Michaels or Oxford for the weekend.

St. Michaels

In St. Michaels, make your reservation at the Harbour Inn Marina and Spa to be completely spoiled. They even have an on-site spa that offers massages, facials, and various body treatments. Rooms start at $250/ night. The Inn at Perry Cabin Resort is another great option, offering rooms overlooking the bay for $360/ night. Rent an entire cottage right outside the center of town for $130 or this Tilghman Island Oasis for around the same price.

After a day of being pampered, walk less than 10 minutes into downtown to have a late brunch at Crepes by the Bay. We heard that the crab and spinach crepe is the best, but try it out and let us know.

For rum, vodka, or gin lovers, Lyon Distilling Company is your place to be. They are within a short walking distance and offer tastings from 11am onwards, with a special behind-the-scenes tour everyday at 2pm, with Saturdays having an additional tour at 4pm. Private tours are available via reservation.

Is your bride-to-be more of a wine-o? Spend an afternoon at the St. Michaels Winery. Known on the shore for their exquisite selection of 18 different wines, they offer samples for only $1 per taste. Private group tastings for 10-20 guests happen daily from 11am-Noon, but be sure to call ahead to reserve your party a spot. Depending on the season, the winery may offer sangria or mulled wine, in addition to the classics. Find something you want to take home? No problem- The venue lets you leave your bottles there while you explore town or go shopping.

For dinner options, 208 Talbot and Bistro St. Michaels both offer fine dining. If you’re craving something more casual after a long day of fun, Ava’s Pizzeria & Wine Bar is the place to be.


Oxford, similar in feel but a bit quieter, offers a great alternative for a weekend with the girls. Stay at Sandaway Suites & Beach for around $280/ night or this cute Airbnb for only $150 (It fits eight people!). Most of their rooms are waterfront; Overlooking the Tred Avon River, Choptank River, or the Chesapeake Bay. The free breakfast showcases food from local farmers and can be enjoyed overlooking a private beach.

If you’re thinking to visit Oxford as a day trip instead, your group can rent bikes from in St. Michaels and take the ferry across the river. While in Oxford, take advice from Tripadvisor and visit the Highland Creamery to try one of the top five ice cream shops in the country. After working up an appetite biking around this charming town, stop by the Robert Morris Inn or Latitude 38 to experience fine dining. For seafood and wine especially, try out Pope’s Tavern at the Oxford Inn. Whether you’re in Oxford or St. Michaels, get your caffeine fix at Rise Up Coffee Roasters.

Just passing through town on your way to a one of Maryland or Delaware’s beautiful, beaches? Discover our favorite bachelorette party spots and activities in Rehoboth, Dewey and Bethany Beaches at Bashelorette OC.