Shoulder season getaways to take before summer kicks off
Visitors can try kayaking in Virginia Beach. Credit: Back Bay Kayaking
Sometimes, in between is the sweet spot. In travel, the shoulder season is just that. The period before the official start of summer is a good time to hit the road. Typically, there are fewer crowds, prices tend to be lower for accommodations and attractions before the summer peak season.
It's not too late to plan a shoulder season getaway. Here's where to go by car, plane and train.
Madison, Connecticut

Explore the hiking trails at Hammonasset Beach State Park. Credit: Alamy Stock Photo/Alamy
DRIVING DISTANCE FROM MELVILLE: Driving distance is about two hours away
If you're looking to stay closer to home, head to this charming Connecticut town. Shoulder season on the Connecticut shore, you can expect less traffic, fewer crowds and lower prices for accommodations than in peak season.
Comb the beaches like the one at Hammonasset Beach State Park, that’s free for in-state registered vehicles, $22 for out-of-state vehicles on weekends and holidays and $15 on weekdays, $7 after 4 p.m. Madison is also home to parks, one favorite is Salt Meadow Park with hiking trails and a dog park. Madison has coastal routes ideal for biking for travelers looking for an adventure. For a bit of exercise and an art fix, walk the Sculpture Mile, a free outdoor art exhibit. See if your visit coincides with a field to table dinner at Field House Farm (June 6). You don’t want to go to Madison without spending time at RJ Julia Booksellers. There’s always something happening, like events showcasing famous authors. Browse for that perfect book or hang out in their cafe. Madison offers historic homes, boutiques, ultra local restaurants and chill vibes.
Check into the Madison Beach Hotel, originally built in the 1800s. Today, it's a beauty by the beach, home to the Sound of the Sea Spa and just a mile from downtown. Room rates start around $425 per night.
More info visitmadisonct.org
Mad River Valley, Vermont

The Pitcher Inn in Warren features a restaurant, a cozy tavern and a wellness center. Credit: The Pitcher Inn
GETTING THERE: Driving distance is about five hours and 30 minutes away
You can’t go wrong with the Mad River Valley in Vermont’s Green Mountain National Forest region. Unlike summer and fall, during the shoulder season Mad River Valley (primarily made up of Warren, Waitsfield and Fayston, often called the three valley towns) is serene. Take a guided tour with Vermont Capital Fishing. They’ll meet you at a location based on where you’re staying. Lakes are there for exploring via kayak and tubing. Clearwater Sports offers kayaking and tubing tours.
The temperatures are ideal for hiking and biking past waterfalls, forests and farms. If foraging is your thing, morels and fiddlehead ferns await your picking. You don't want to miss the Warren Store for local beer, wine and other goodies.
You’ll feel at home at The Pitcher Inn, an intimate (11 individually designed rooms and suites) luxurious inn. Get cozy at Tracks Tavern, their pub overlooking gardens and a brook and enjoy farm-to-table cuisine at their restaurant 275 Main. Treat yourself and stop in their wellness center that’s in a historic farmhouse. Take advantage of The Pitcher Inn’s spring shoulder season package, with 20%-25% discounts off two- and three-night stays, with culinary and wellness experiences included. Room rates start at $600 per night.
More info visitmadrivervalley.com
Virginia Beach, Virginia

Beachgoers swim, surf and lounge in Virginia Beach. Credit: AP/Steve Helber
GETTING THERE: Driving distance is about seven hours away; Travelers can take Amtrak from Penn Station (eight hours; round trip starting at $150)
Shoulder season is one of the best times to visit this coastal city. The weather is mild, you can enjoy the oceanfront, the 3-mile boardwalk, parks and preserves without the summer crowds. Oceanfront Beach is free and where you’re likely to hear live music and see street performers.
There are numerous concerts and festivals in May and June including Neptune Spring Wine Festival (May 16), Dave Matthews Band (Veterans United Home Loans Amphitheater on June 6) and JazzTeenth Festival (June 20). It’s also a great time for kayaking and boating. Fishing charters head out on the Atlantic for what can be the most rewarding catches of the year to reel in flounder and cobia as both species hit peak season through May and June. Rudee Tours offers fishing expeditions in the area. Visitors can choose from a variety of boating trips including fishing, wildlife (dolphin and whale watching) and sunset cruises.
There are many options for accommodations, try Delta Hotels Virginia Beach Waterfront Suites on Chesapeake Bay. Rates start at around $360 per night.
More info visitvirginiabeach.com
Gulf Shores/Orange Beach, Alabama

People paddleboarding during the Flora-Bama Gulf Coast Paddle Championship. Credit: Gulf Shores & Orange Beach Tourism
GETTING THERE: Fly from Kennedy on United, Delta and American on flights to Mobile, Alabama, and make the scenic one-hour drive to Gulf Shores.
When you think of Alabama, beautiful beaches may not be the first thing that comes to mind. Think again: Gulf Shores/Orange Beach with its white sand and turquoise waters rivals Florida’s finest. Better still, you won’t have to be strategic about finding a spot because there aren’t big crowds, especially during the shoulder season.
In addition to the beach, you get golf, biking, paddleboarding and boating at Gulf State Park, with its trails and wildlife. The Hammock Time Tiki Tour is a hoot, a pontoon boat with two double hammocks and a tiki bar. Guests can sip cocktails and may even spot dolphins during the excursion.
Jesse’s on the Bay is the talk of the town with it shrimp and grits with Conecuh sausage and smoked Gouda bayou Cora grits and the Atlantic Sea scallops with crème brûlée cornbread, Tasso bacon, dandelion gremolata and more. Another favorite is longtime, family-owned DeSoto’s Seafood Kitchen — casual, homey, beloved for its crawfish étouffée, crabcakes and sweet potato casserole.
Of course, you have all the water sports you can handle. There is plenty of kid-friendly spots like the Alabama Gulf Coast Zoo that’s not only animals, but rides and ziplining too. Play mini golf at Pirate's Island Adventure Golf. Gulf Shores is a place that won’t break your budget.
Here, you have a variety of accommodations — from the new Embassy Suites by Hilton Gulf Shores Beach Resort, right across from the beach. Room rates start around $550 per night.
More info gulfshores.com
IF YOU GO
Madison, Connecticut
Hammonasset Beach State Park, 1288 Boston Post Rd., 203-245-2785, ctparks.com
Salt Meadow Park, 1362 Boston Post Rd., 203-245-5623, madisonct.org
Sculpture Mile, Main Street, 860-938-7154, ctvisit.com
Field House Farm, 623 Green Hill Rd., 203-779-9187, fieldhousefarm.net
RJ Julia Booksellers, 768 Boston Post Rd., 203-245-3959, rjjulia.com
Madison Beach Hotel, 94 West Wharf Rd., 203-245-1404, hilton.com
Mad River Valley, Vermont
- Vermont Capital Fishing, company goes to the location; 802-370-0491, vermontcapitalfishing.com; Rates for a half day excursion (four hours) is $250 for the first guest, $100 for each additional guest, with a three guest maximum
- Clearwater Sports, 4147 Main St, Waitsfield, 802-496-2708, clearwatersports.com; Starting at $95 with a four-person minimum for a guided kayaking tour and $38 per person for tubing
- Warren Store, 284 Main St., Warren, 802-496-3864, warrenstore.com
- The Pitcher Inn & Wellness Center (Tracks Tavern and 275 Main), 275 Main St., Warren, 802-496-6350, pitcherinn.com
Virginia Beach, Virginia
- Oceanfront Beach, 1700 Atlantic Ave., 757-385-4700, visitvirginiabeach.com
- Rudee Tours, 200 Winston Salem Ave., 757-425-3400, rudeetours.com; four hour fishing trip $53, $47 for kids
- Delta Hotels Virginia Beach Waterfront Suites, 2800 Shore Dr., 757-481-9000, marriott.com
Gulf Shores/Orange Beach, Alabama
Gulf State Park, 20115 State Park Rd., 251-948-7275, alapark.com
Hammock Time Tiki Tour, 28101 Perdido Beach Blvd., Orange Beach, 251-253-2430, hammocktimetikitours.com; two hour Island Tour is $70 per person
Jesse’s On The Bay, 1631 Crosswinds Ct., 251-965-3827, jessesrestaurant.com
DeSoto’s Seafood Kitchen, 138 W. 1st Ave., 251-948-7294, desotosseafoodkitchen.com
Alabama Gulf Coast Zoo, 20499 Oak Road East, 251-256-7008, alabamagulfcoastzoo.com; $23.95, $15.95 ages 3-12
Pirate's Island Adventure Golf, 3201 Gulf Shores Pkwy., 251-968-4653, piratesislandgolf.com; $16, $12 ages 4-12
Embassy Suites by Hilton Gulf Shores Beach Resort, 112 W. Beach Blvd., 251-200-4644, hilton.com