Global Staci

When an invitation to a mid-July wedding celebration came, I knew right away we’d attend and make a long weekend getaway of it. First, I investigated how we’d get there—Amtrak from Baltimore to Bridgeport. It was almost even money with driving and none of the hassle.

Next, where to stay? I chose the only hotel I could find right on the beach, a short Uber away. Both my husband and I thoroughly enjoyed exploring the area without a car and recommend this itinerary as a fun and relaxing break for couples or friends.

I’d not spent more than one night in Connecticut my entire life, so this was uncharted territory. I’d never heard of Lordship, and certainly never heard of Point No Point, the beach along the Long Island Sound where The Surfside Hotel lives. The entire area is part of Stratford, Fairfield County, a part of Greater Bridgeport.

[PRO TIP: Although we didn’t have any trouble actually getting a rideshare, I recommend leaving yourself at least 15 minutes to order the car and allow it time to reach you.]

Day 1 | Arrival

Our train arrived after the check in hours at the hotel, so we got instructions for the lock box, dropped our bags in the room and went straight to Little Pub, the onsite restaurant and bar open for lunch and dinner. Inside the hotel, Room #5 offers complimentary coffee, tea, and water 24 hours a day. We slept soundly, as the Tuft and Needle® beds are luxuriously comfortable.

Day 2 | Exploring Lordship

Relaxing on the outdoor patio of our room in the morning with a hot cuppa coffee was all we needed; there’s no easy breakfast joint nearby. Once we got a bit peckish however, we decided to get our bearings and see the neighborhood by walking to Lordship Corner Market which sells sandwiches, salads and ice cream in the summer as well as snacks and beverages.

[PRO TIP: For an espresso drink and pastry treat, visit The Drowsy Whaler the mobile coffee and grog trailer, in the parking lot across from Surfside. They make fabulous coffee drinks and delicious baked goods.]

Satiated, we went back to the Surfside, signed the online activities waiver and took out the bikes. With miles of flat scenic roads, Lordship is a great place to get outside, especially when the weather was as ideal as it was for us in July. Riding along the shoreline is great; there is very little car traffic. The area is easy and safe to navigate; just look at a map before you set off and you’ll be fine.

We biked to Stratford Point to check out the Connecticut Audubon’s preserve, a 28-acre coastal habitat jutting into Long Island Sound and the mouth of the Housatonic River estuary. The coastal habitat showcases grasslands and shrubs, salt marsh, a pebbly beach, and a coastal trail with panoramic views of the water. It attracts scores of migratory songbirds, waterfowl and other marine life, not to mention locals fishing from the shores. The new preserve is open to the public from 9am to 4pm.

Right next door is the historic Stratford Point Lighthouse, guiding mariners past the shifting sand bars at the mouth of the Housatonic River into Long Island Sound since 1822. The lighthouse was added to the National Register of Historic Places in 1990 and is used for housing by the US Coast Guard.

It was nearly 4pm and time to head back to Surfside to drop off the bikes and head to Riley’s, a local spot on the seawall with an outdoor patio, and food and drink deals at happy hour. Keeping it super local, we enjoyed dinner at Little Pub, then sat on the beach for sunset.

[PRO TIP: I’d read about the Concerts at Park City Music Hall, an intimate live music venue serving up regional acts, and put it in the pocket as an option for Friday evening. We didn’t go, but being only a few miles away, it seems like a great option for those without four wheels.]

Day 3 | Lordship Take II

Feeling braver than yesterday, we ventured out further on the bikes today, this time toward the northern part of the peninsula to check out Mellow Monkey gift emporium. Just down the road is The Landing at Five Twenty, offering American cuisine with a Japanese twist with a large waterfront patio. We had just enough time to get back to Surfside and get cleaned up for the main event.

The celebration that evening was at the waterfront restaurant Boca Oyster Bar in Bridgeport, a short Uber ride away.

Day 4 | Keeping It Royal

Our late afternoon train departure gave us time for two things: kayaking and brunch. In addition to the bikes, Surfside guests can use kayaks and paddleboards, free of charge. Because the water wasn’t calm enough for SUP, we opted to take out individual kayaks, a fantastic choice.

Having checked out, bags in tow, we opted to eat near the Bridgeport Train Station at Queen’s Delight. Not only was this casual city restaurant just a couple blocks from the station, the grits and biscuits were among the best I’ve ever tasted.

[PRO TIP: The Surfside honored my request for a late check out, noon instead of 11am, but for an extra $25 you can leave your room at 1pm.]