The Surfside local guide · Stratford, Connecticut
A little exploring.
A lot of unwinding.
Start with a walk by the water. Spend an afternoon browsing a harbor town, visiting a local farm shop or making time for a massage. Then come back to dinner at Little Pub and a comfortable night at Surfside.
There’s plenty to discover—and plenty of room to do very little.
01 · Set your own pace
Stay close. Slow down.
Leave a little space in the day for the shore. Take a stroll along the Lordship seawall, watch the water, then settle in for something good to eat.
Little Pub in the lobby
Your easiest dinner plan is right downstairs. Gather over burgers, comfort food and a bowl of soup, or make lunch part of a leisurely day by the water.
Lordship Corner Market
Pick up a breakfast or lunch sandwich before a little neighborhood exploring. A useful local stop when your biggest plan is a slow morning.
Milford Point Coastal Center
Bring binoculars—or simply your curiosity—for marsh views, observation platforms and short trails. The sanctuary is open year-round, dawn to dusk; the visitor center has separate hours.
Dal Mare Pizzeria
Pick up a pizza next to Lordship Corner Market. Add a grinder or salad and make it an easy neighborhood dinner.
Riley’s by the Sea
Head down the street to Riley’s by the Sea for seafood and a meal by the water. A relaxed stop along the Lordship seawall.
The Windsock
Head to The Windsock for a late night game of pool and a little neighborhood atmosphere. This laid-back local spot sits beside the airport.
Mellow Monkey
Our pick for the best in unique gifts. Browse Mellow Monkey for quirky finds, home accents and something unexpected to take home.
02 · Make an afternoon of it
Two towns worth wandering.
Drive into town, park, and explore on foot. Fairfield brings shops and a night out; Milford pairs a classic town green with a harbor stroll.
An afternoon in Fairfield
Start around Sherman Green and the Post Road, where boutiques, cafés and gift shops give you plenty of reasons to linger.
- Browse: The Beehive at 1499 Post Road for home accessories and gifts, then explore the surrounding downtown shops.
- Pause: Take a coffee break or a leisurely lunch before your next stop.
- Stay for the evening: Check Fairfield Theatre Company’s StageOne and The Warehouse calendars, or see what’s on at SHU Community Theatre.
An afternoon in Milford
Begin at the downtown Green, browse the shops around Broad and River Streets, and leave time to wander toward Milford Harbor.
- Take it slowly: Coffee, a little shopping and a harbor walk make an easy afternoon.
- Add some culture: Look for an exhibition, performance or event at the MAC near the train station.
- Make it seasonal: Check the downtown event calendar for festivals and holiday happenings during your stay.
03 · A little time for you
Put unwinding on the itinerary.
A massage, a yoga class or an afternoon at the spa fits nicely between a slow breakfast and dinner back at Surfside. These are independent local providers; book directly ahead of your stay.
Tranquility
Choose a massage, facial or body treatment at Tranquility Mind & Body Wellness Spa. An easy way to make a getaway feel like a real break.
Re:mind Wellness
Explore massage, an infrared sauna, salt-room sessions and scheduled workshops. Couples’ massage is also on the menu for a shared afternoon off.
Yoga4Everybody
Build a yoga class into your Fairfield outing. Check the current schedule, class level and booking details to find a session that suits you.
04 · A taste of Connecticut
Local pours. A change of scenery.
Pick one stop and make time to enjoy it. Check opening hours and tasting availability before you go, and arrange a ride when drinking.
Two Roads & Area Two
Explore Two Roads’ brewery campus, with tasting rooms, Area Two’s experimental beers and a food hall. A close-to-home choice for a relaxed afternoon.
Dockside Brewery
Pair a local beer with a meal at this waterfront brewery in Devon. Check current seating and reservations; outdoor spaces depend on the weather.
Jones Winery
Head inland for a Connecticut wine tasting at Jones Family Farms, where a historic dairy barn sets the scene. Consult the winery’s calendar before planning your country afternoon.
05 · Country roads & something to take home
Farm shops. Market mornings.
A pie for later, cider doughnuts for now, and a few local finds to bring home. Farm visits change with the season, so plan around what’s open.
Silverman’s Farm
Browse cider, pies, produce, local honey and other farm-market favorites. The farm currently lists its 2026 market and animal-farm season through December 31; holiday hours vary.
Beardsley’s Cider Mill
Stop at the farm store for cider, pies and cider doughnuts. Apple picking has finished for 2026, but the store’s posted season continues through Christmas Eve.
Shop what’s local
Plan a market morning around your dates. Fairfield has summer and winter markets; downtown Milford’s outdoor farmers market is seasonal and has closed for 2026.
Borrow one of our plans
Three easy ways to spend a stay.
A quiet weekend
A slow breakfast, a Lordship seawall stroll and a good book. Add Milford Point if you feel like exploring, then come back for dinner at Little Pub.
Shops, spa & the harbor
Book a Milford massage, leave time for coffee and downtown shopping, then wander toward the harbor. Keep the evening open for a relaxed night back at the hotel.
Cider & country roads
Visit Beardsley’s farm store, then add White Hills when its tasting room is open—or plan your afternoon around Jones Winery. Check the season and arrange transportation before setting off.