The land comprising Woolwich Township belonged to the Huron Nation and then to the Mohawk Nation. The first European settlers arrived in Woolwich Township in the late 18th century. The early settlers were primarily from England or Ireland until about 1830.
In 1806, the major portion of this tract was sold to Mennonites from Pennsylvania, the so-called Pennsylvania Dutch (actually Deutsch or German). A community by the name of Bristow's Corners was already in existence in 1839 when a post office was assigned there. Local merchant Samuel Weber had been visiting New York State in the early 1850s and was apparently impressed with Elmira, New York. This may have been a factor in the decision of Woolwich Township council in 1853 to rename the community Elmira.
In addition to Mennonites from Pennsylvania, the majority of settlers were from Germany by the 1850s. Railways arrived in the late 1800s: the Grand Trunk and the Canadian Pacific. Furniture manufacturing and other industries began to open.
- From Guelph, take Elmira Road north. This becomes Wellington County Road 86 north of the city and later Waterloo Regional Road 86. This becomes Church Street in Elmira.
- From Kitchener-Waterloo, take the Conestoga Parkway north, which becomes Waterloo Regional Road 85 north of the city. Regional Road 85 takes a left turn just south of Elmira; continue straight (on Arthur Street, Regional Road 21) to reach the town centre.
- 1 Waterloo Central Railway, 155 Howard Ave, ☏ . The WCR offers a seasonal tourist service running a train of historic passenger cars, and a historic steam or diesel locomotive servicing 5 stops between Waterloo and Elmira. See the St. Jacobs article for details.
By car; the main street, running roughly north-south, is Arthur Street (Regional Road 21). The main east-west cross street is Church Street (Regional Road 86).
Elmira is small enough to walk between any places on foot.
The Waterloo Central Railway operates a seasonal tourist train from the St. Jacobs Market. During the Elmira Maple Syrup Festival, the WCR extends train service to downtown Elmira; otherwise, service ends at Oriole Parkway East in Elmira.
- Elmira Theatre Company (firstname.lastname@example.org), 76 Howard Ave, ☏ , toll-free: . Community theatre. 3 shows, including 1 dinner theatre a year.
- 1 West Montrose Covered Bridge (Kissing Bridge), Covered Bridge Drive, West Montrose (south of Line 86 in West Montrose, 7 km east of Elmira). Built in 1880–1881, it is Ontario's only covered bridge (excluding recent construction such as the timberframe pedestrian covered bridge in Guelph).
- The Elmira Maple Syrup Festival, held annually in late March or early April, attracts 60,000 visitors and is world's largest one-day maple syrup festival. The festival features sugar bush tours; a half-mile long outdoor mall with vendors of local speciality food and crafts; a craft show; the Mayor's Maple Syrup contest; and pancakes and golden maple syrup.
- Elmira Golf Club, 40 Eldale Road, ☏ . 18-hole golf course, practice facilities, shop stocked with the latest golf products, the Grill on the Green with home cooking.
- Kitchen Kuttings Inc., 2 Arthur St S, ☏ . Tu-Th 9AM-6PM (and M in Dec), F 9AM-8PM, Sa 9AM-5PM. A specialty food store with an assortment of homemade jams, pickles, preserves, Canadian and imported fresh-cut cheeses, homemade summer sausage, old fashioned fudge, brittle and a range of specialty local food.
- Elmira's Sip 'n Bite, 39 Arthur St S, ☏ . All-day breakfasts, and other diner food.
- The Grill on the Green, 40 Eldale Road, ☏ . Freshly made wraps, burgers, sandwiches, fresh cut fries, daily homemade soup.
- Elmira Tandoori Grill, 16 Arthur St South, Unit #3, ☏ . M-Th 11:30AM-2:30PM, 5-9PM; F Sa 11:30AM-2:30PM, 5-10PM, Su 4-9PM. Indian cuisine. Dishes $11-17, set meals $19-22 per person.
- The Central Tavern, 30 Arthur St S, ☏ . F Sa noon-2AM, M-Th 4PM-midnight. Sports bar with pool tables serving pizza, wings, nachos, etc.
- Leisure Estates Bed & Breakfast Retreat, 1099 Floradale Rd., ☏ , toll-free: . On a park-like 50-acre wooded estate, groomed trails leading through the trees to the adjoining town of Elmira (10-min walk). Private entry, sat TV, DVD, free phone and Wi-Fi, central air; shared kitchen, dining, living room on lower level, generous full breakfast; four rooms with private en suite baths, fireplaces. From $139.
St. Jacobs hosts one of Canada's largest year-round farmers' markets and is about 7 km south of Elmira.