Wallingford, CT City Guides



1. High Meadow

City: Wallingford, CT
Category: Accommodations
Telephone: (203) 269-2351
Address: 1290 Whirlwind Hill Rd.

Description: This house is ancient, constructed in 1742, but has been moved from its original location in Branford up the road to a farm in Wallingford. Once it was known as the Jonathan Towner Half Way Tavern, a popular travelers’ stop between New York and Boston. Since 1975 it has served the same purpose here among meadows in Wallingford. There are 3 rooms in the main house, one of which is decorated in a fascinating “Thai” manner and the others more traditionally. You can also stay in Brae Cottage, a small home in an open field overlooking a pond, with a fireplace, terrace, kitchen, dining room, and bathroom with whirlpool tub and shower. It even has its own washer and dryer, and is the perfect place for a long stay here in central Connecticut. Your location on Whirlwind Hill puts you right between two of Connecticut’s vineyards, so you should certainly stop at one (or both) on your travels from High Meadow.

2. Wallingford Victorian Bed And Breakfast

City: Wallingford, CT
Category: Accommodations
Telephone: (877) 269-4499
Address: 245 N. Main St.

Description: For the last 10 years this beautiful Victorian house in Wallingford has been welcoming guests to its large rooms. You can walk into the center of town here, or jump onto the Merritt or I-91 to reach New Haven or Hartford easily. There are 3 rooms in the house currently available, each with its own amenities. The Samuel Suite has a Jacuzzi and private entrance. The Georgianna Suite includes a sitting room and work area in the tower, as well as a private balcony. The Margaret Room can be joined to the Georgianna for a family suite. Owners Jeff and Brenda also run a furnished condo unit a mile away by the railroad station; with 2 bedrooms, it’s the perfect place for a longer stay, available by the week or month.

3. Neil’S Donuts

City: Wallingford, CT
Category: Restaurants
Telephone: (203) 269-4255
Address: 83 N. Turnpike Rd.

Description: Connecticut loves its donuts. This is evidenced by the fact that there are at least twice as many Dunkin Donuts as its nearest chain fast-food competitors in the state. However, there are also some great local donut shops, and Neil’s is one of the best. The chocolate-covered sprinkle donuts are leagues ahead of the fast-food competition. However, it is the old-fashioned donut that is startling: It is either the way donuts used to be or some new fantastic creation. For those of us used to the little old-fashioned “rock” donuts you get at the chains, there is a sudden understanding of their appeal. Make sure to get them warm in the morning, and crunch through the outer crust into the dense and chewy layers, making sure to dip them in your hot coffee. Neil’s also bakes cookies, pies, coffee rolls, muffins, croissants, and Danishes, as well as a selection of breakfast sandwiches. But as I said, this is a donut-loving land, and Neil’s is for the true connoisseur.

4. Gouveia Vineyards

City: Wallingford, CT
Category: Tours & Attractions
Telephone: (203) 265-5526
Address: 1339 Whirlwind Hill Rd.
Insider Pick:

Description: Established in 1999, this winery brings the Portuguese heritage of its owner, Joseph Gouveia, to the Wallingford Hills. You’ll pass farm silos and fenced pastures on the way to Gouveia Vineyard, just past the Mackenzie Reservoir. With 140 acres, Gouveia is one of the largest vineyards in the state; 15 acres are planted, and there’s plenty of room to expand. The tasting room is a gorgeous stone structure, and visitors flock to the site year-round. Inside, high wood beams frame the larger of two rooms, greenhouse-like windows shape the side walls, and a double-sided fireplace warms patrons in winter. In warmer months, you’re likely to see picnickers on the lawn and on the patio under the pergola, sipping Stone House Red and sharing cheese, sandwiches, or possibly a birthday cake. The winery is equally beautiful in winter, as late afternoon light reflects off the snowy vines. Gouveia offers a wide range of wines, including whites like Seyval Blanc, Cayuga, and two styles of Chardonnay. For reds, try the Cabernet Franc, which is rich and earthy, or the Merlot, with a hint of spice. Open Thurs through Sun.

5. Paradise Hills Vineyards

City: Wallingford, CT
Category: Tours & Attractions
Telephone: (203) 284-0123
Address: 15 Wind Swept Hill Rd.

Description: One of the newer wineries in the state, Paradise Hills sits on 65 acres in the beautiful Wallingford Hills, an easy jump from nearby Gouveia Vineyards. Paradise Hills has a small but varied selection of reds and whites, including Chardonnay. The owners have been growing grapes for 25 years, and opened the Tuscan-style tasting room at the end of a cul-de-sac in 2011. You’ll feel as if you stepped into an Italian landscape painting. The ambiance, inside and out, is elegant and airy, and you’re sure to admire the copper bar and patio as you relax and sip. The historic Washington Trail passes through the property, and a red and white blend are both named for it. Also honoring that famous trail that General Washington traveled on through Wallingford is President’s Choice, a red blend made with Cabernet Sauvignon, Merlot, and estate-grown Chambourcin. The tasting room is open Thurs through Sun.

6. Oakdale Theatre

City: Wallingford, CT
Category: Tours & Attractions
Telephone: (203) 265-1501
Address: 95 S. Turnpike Rd.

Description: The current title of this theater is technically Toyota Presents the Oakdale in Association with Comcast, but no one actually calls it that. “The Oakdale” opened in 1957 as a tent in an alfalfa field, and in 1972 was upgraded to a 3,000-seat theater in the round with a slowly spinning stage. Today the new 1996 theater is the largest in the state of Connecticut, and has gone through a variety of corporate sponsorships. The theater hosts Broadway shows, comedy performances, and (mostly) popular music concerts featuring rock, hip-hop, and country stars. The Oakdale is wheelchair accessible and is nonsmoking, although there is a designated area for it. There are concessions, and beer and wine are available. The best seats by far are the “red” loge seats at the front of the balcony. Get them if you can!

7. Rap-A-Pony Farm

City: Wallingford, CT
Category: Tours & Attractions
Telephone: (203) 265-3596
Address: 995 North Farms Rd.

Description: Catering to beginner riders, Rap-A-Pony Farm has been running for 20 years, teaching children (of all ages) English and Western riding techniques. They have school vacation and summer programs for very reasonable prices if you want to learn the care and riding all in 4 days. Otherwise, they have 1-hour group lessons, where they teach you how to tack and ride properly, or half-hour private lessons (which, of course, can be extended). Rap-A-Pony has indoor and outdoor arenas, so you can even go on a rainy day or in cooler weather. They provide helmets, but be sure to wear sturdy shoes and clothes.
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